“Not for sale” acquisition advice on small commercial property
Property: small commercial building in mid-Atlantic region. 6 units under one roof, at about 5,000 sqft each. Current tenants include auto repair/maintenance and automotive custom work.

Situation: For personal and business reasons, I’d like to purchase this building although it’s not listed for sale.

I visited the building last week because I happen to know one of the tenants. While I was more closely looking at the external building features, the property manager came out and invited me to tour a smaller, 2500 sqft vacant unit. Since the person assumed I’d just be a renter… I just went with it rather than immediately mentioning my purchase interest. Im younger and inexperienced so didn’t want to fumble the ball before even playing the actual game

Anyways, we left it with a couple facts that I discovered
1. The owner is old (94) and has downsized portfolio over the years 
2. The owner has a daughter… I’m not sure if they’d expect to take over or not
3. The property manager has worked with the owner for 30+ years

I’m reaching out to this community to ask: “how would you play this?”

A direct route could be to simply call the property manager and ask if they would entertain any offers

Another way could be to ask for a meeting with the owner to learn more about the vision/direction of the building and it’s ownership

Hoping someone with some experience in acquisitions can challenge me to think about this in a different way or offer potential routes to success.
[{"id": "ho5gkh6", "text": "Call them up and ask them if they are interested in selling.", "replies": [{"id": "ho8t3gl", "text": "And 2) Be cognizant that the property manager's employment likely depends (at least in part) on managing this building. Letting him/her know that you'd like to maintain the same management should be helpful. 3) If/when you get to talk w/ owner, I'd ask his/her story about how they built their portfolio. Also see if there are any others that could also be for sale 4) If prepping offer, agent and comps. Esp. comps that the owner previously sold", "replies": [], "depth": 2}], "depth": 1}, {"id": "ho5hmpt", "text": "Whenever in doubt.\n\nKeep it direct and keep it honest.", "replies": [], "depth": 1}, {"id": "ho5j1eq", "text": "Be direct and ask if the Landlord would be interested in selling the property.  My office receives cold calls to purchase my properties regularly.  It's annoying.  However, be direct and to the point.  Don't waste people's time.  It's either \"Yes/Maybe\" or \"No\".\n\nKeep in mind there are many reasons not sell property.  For one, if a Landlord doesn't need the capital there's no place to park the funds.  Then there's tax.", "replies": [{"id": "ho5pniv", "text": "And when you're trying to buy a property the owners have no reason to sell, expect to pay a premium.  But that said, sometimes it's still totally worth it to get that particular building at a premium price if it'll help your own business.", "replies": [], "depth": 2}], "depth": 1}, {"id": "ho5nfbh", "text": "The property manager would be irresponsible not to forward any offer. Send a letter to the PM, addressed to the owner (very easy to find out who that is) asking if said owner would be interested in selling.\n\nThe owner is 94, he's been downsizing his portfolio and, clearly, attempting to minimize the tax impacts of real estate on his children.\n\nHave financing in order.  Don't go in cold.  Know your values, and what you can not only afford, but what the bank will loan you.", "replies": [{"id": "ho5tzhw", "text": "I would also be prepared to budget for a phase 2 subsurface investigation. As a phase 1 inspector, just based of your brief description, I would most likely recommend a phase 2", "replies": [], "depth": 2}], "depth": 1}, {"id": "ho5x9ds", "text": "Two things could hold back the deal. Buyer could be only wanting to sell a couple properties a years that triggers capital gains so let them know you can be flexible on closing timing of they are trying to do a 1031 exchange. \nAlso property management business could be concerned about losing good revenue as the owner downsizes so mention you would consider keeping management in place of you were to buy the property. That could help them forward along your offer quicker.", "replies": [], "depth": 1}, {"id": "ho7e91f", "text": "A tactic I\u2019ve used is to find a like kind property that they may want to 1031 exchange into if they are willing to sell. It can entice them into wanting to entertain your offer.", "replies": [], "depth": 1}, {"id": "ho7g2zm", "text": "Contact the owner, not the PM. PM may or may not pass on your offer (and likely won\u2019t pass it on if it\u2019s not an actual written offer). Even if they pass it on, they\u2019ll add their commentary or, if the owner seems receptive to selling, reach out to other buyers/get it listed.", "replies": [], "depth": 1}, {"id": "ho7oear", "text": "I would certainly be telling the property manager they could keep their job before asking them to float whether seller would sell.", "replies": [], "depth": 1}, {"id": "hobdm28", "text": "Call the owner directly. No need to talk to property management company until it's time to see the rent rolls.", "replies": [], "depth": 1}, {"id": "hoh45xc", "text": "A broker in the area may know history on the owner or building. If cold call the owner directly and ask if they would sell and name what you\u2019re willing to pay. These things (especially rented out and cash flowing) usually will only entertain above an market sale. Less conditions the better. Get your financing lined up.", "replies": [], "depth": 1}]