Yes, you have to look long term, and yes, rents should go up over time.You can find plenty of stories of tenants not paying rent for 12-18 months straight during Covid, eviction moratoriums, and you get the joy of repairing the property, ensuring heat/water/functionality with the threat of legal action from the city/county for non compliance, despite non payment.Do what’s best for you-planning to lose money on REI, regardless of length of time, isn’t best for me, so I would recommend to keep searching, or restructure the deal in your favor.

That said, the BEST way to assure all that horror doesn't happen, is by keeping things as thorough as humanly possible; detailing directives, pre-agreed, for literally any and every potentiality in life, AND keeping things simple. 

He kept assuring me he would take care of it and never did.

Every one keeps talking of global warming; EV industry keeps talking of green energy when electricity is generated by n large using fossil fuels, n no of startups keep claiming solutions to reducing carbon footprints with Building designs which are adherence to compliance and essential environmental standards.

At this point, this is a retirement diversification move for us to try and have some extra passive income when we retire in 13-15 yrs.I guess the big magic crystal ball question I have is, how can I best assure (in an unsure market and world) that my offers aren't too high and I'm not overpaying for my local market, and won't wind up upsidedown in value? 

Imagine your banker going in front of a loan committee at the bank which includes their bosses, colleagues with their own deals and compliance officers.

Also be sure you are in compliance with local laws.

Property management is my primary focus, providing full management services including tenant placement, rent collection, lease contracts, accounting, eviction assistance, and insurance compliance. . 

If the real estate commission determines guilt, the commission can impose a fine not to exceed (a) $1000 per day that the individual is not in compliance with the statute, or (b) the amount of money earned by the person in violation, whichever is greater. 

I have about 55 doors I'm looking after and run a full time construction company as well as a landlord website so I can assure you I don't do it because I have free time laying around But i do have much more of a handle on what's going on in my property.