He assures me that he will have someone out yesterday and have the report by today to make closing on Monday.Murphy’s law ever present, the new appraiser says no one was home for the appraisal so she wasn’t able to complete it.My lender said he put out 45 bids for another appraisal but the earliest anyone is saying they can have it submitted is April 13th.

But can't get an answer from one on how they are doing this in compliance with their broker's agreement?

above.Form 1099-S: Proceeds from Real Estate Transactions is generally issued by the real estate closing agent—a title company, real estate broker or mortgage company.To avoid getting this form (and having a copy sent to the IRS), you must give the agent some assurances at any time before February 15 of the year after the sale that all the profit on the sale is tax-free.To do so, you must assure the agent that:You owned and used the residence as your principal residence for periods totaling at least two years during the five-year period ending on the date of the sale of the residence.You have not sold or exchanged another principal residence during the two-year period ending on the date of the sale or exchange of the residence.No portion of the residence was used for business or rental purposes by you or your spouse.At least one of the following three statements applies: (1) The sale price is $250,000 or less; (2) You are married, the sale price is $500,000 or less, and the gain on the sale is $250,000 or less; (3)You are married, the sale price is $500,000 or less, and:You intend to file a joint return for the year of the sale or exchange.Your spouse also used the residence as his or her principal residence for periods totaling two years or more during the five years ending on the date of the sale.Your spouse also has not sold or exchanged another principal residence during the two-year period ending on the date of the sale or exchange of the residence.Essentially, the IRS does not require the real estate agent who closes the deal to use Form 1099-S to report a home sale amounting to $250,000 or less ($500,000 or less for married couples filing jointly).You should not receive a Form 1099-S from the real estate closing agent if you made these assurances.If you don't receive the form, you don't need to report your home sale at all on your income tax return.If you did receive a Form 1099-S, that means the IRS got a copy as well.

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.