I have been a long-term buy-and-hold investor in both locations for many years.

Holding a tenants hand and talking them through a rent increase is not necessary and not professional .

Looking at some old houses like 1920s or 1950s, I am not sure how much will they hold in the next 30 to 40 years.

Are you planning to create a business entity out of which you with either hold and/or manage this property?

If you did not win a bid, they should have simply returned the cashier's check you provided them or given you a refund if it had already been deposited in their escrow account, unless there was an agreement between you for them to hold it for the next offer.

I could also increase the NOI by taking over management myself.Seller is motivated to sell because he's out of the area and trying to consolidate his holdings for easier management.  

My wife and I are proud buy & hold investors with 4 doors (2 single family, 1 duplex) and are looking to grow as our financing opens up.   

Plus, rallying support from the community and linking up with housing advocacy groups could strengthen your case.

Of course, it is crucial to consult with legal and tax professionals when structuring your business and real estate holdings.

Not sure how to properly tell the tenant who's income doesn't support the rent that I do not want to resign the the lease with her.