In general, if you had net losses from your schedule E rentals (and were not a RE pro), they would be limited to offsetting other passive income only.

With this limited amount of information it sounds like he should sell it. 

I drink work coffee provided for FREE.4. limit my lunches at work to about $2 a meal.

@Riggies B tang it seems that you are not looking for a loan on the conventiknal market which would limit your LTV to 75% and close under your name(you can put it under LLC after closing) which would have the best rates.

I did just that when I began to pack my things at the meeting while he ranted and spouted his limited knowledge of landlord/tenant guidelines.

I don't bother trying to transfer them to my S Corp after closing due the limited risk of having the mortgage called and frankly not wanting to deal with it. 

some of my tenants do not use electronic because of limits the companies like cash app use on their system.

RE investment can help you do that if selected right property but I would invest just for that reason because it always might not work and there are limitations.  1) Depending on your retirement goals, you will be better off with a qualified plan(profit sharing plan) for your S-corp that will shelter more of your income from tax and also lower your AGI.

Assuming that the conditions above are satisfied, wouldn't it be the best option to search for a deal that is as close as possible to the maximum FHA limit, and the one that has 4 units?

Also they may limit your ability to obtain better rate mortgage as you may only have commercial rates available.