In this particular case, we couldn't consider the rent from the third unit because it wasn't legal. 

Nowhere did I write that title companies are great, in fact I'm more aware than most that they're just people in a particular business trying to make a buck. 

This is particularly true for absentee owners.

As a first-time investor, you might find it easier to start with properties built after 1975, as building codes improved significantly around this time, particularly regarding wiring and plumbing, which can reduce the number of surprises and costly repairs.

However, you may be able to capitalize some of these costs, particularly if they relate to improvements or preparation of the property for rental.Expenses (after December 1, 2023):Any expenses incurred starting from when the property was available for rent (December 1, 2023) can be deducted.

Lets just say that $50K has been carrying in losses from this particular property, this means (according to my CPA) that I can only offset $50K from the capital gain of the sale of this one property.

That should make small stuff like roaches and a ceiling light insignificant, particularly if you switch to full time 3rd party management and get out of the details. 

Here are some common structures and terms that have worked well for both private lenders and borrowers in real estate, particularly for those focusing on single-family homes (SFH) and multifamily (MF) properties like you're considering in Philly’s B Class areas.1.

In particular, with a stabilized, cash flowing multifamily what relationship (between the two) makes sense to the buyer and lender?

Affordable housing is not something that they have any say in, as it is regulated by the particular state.