Maybe it would be enough to to satisfy your income requirements.

If you can't find somebody here, you should check them out because as the name states, they are willing to inspect any property you may have and satisfy your checklist. 

(Note: This question is here to help investors who want to maximize liquidity: Say you purchase 2 SFH's that cost $100,000 each, ($200,000 total), and get 2 mortgages with 20% down, ($40,000 in total Down Payments, $160,000 in Mortgages Payable), does this satisfy your reinvestment requirements?

It keeps the units filled and they're satisfied with the retirement income.

I want to be able to make them an offer for their house but it's a challenge for me when the realtor is involved.

Although, the difficulty in finding buildings that will allow (or won't find out) about airbnb'ing can be the most challenging part!  

I completely understand your frustration and am very sorry for the challenges you have encountered. 

It will be a challenge when your SO isn't on board (yet).I am kinda in the same boat, my SO isn't into real estate investing, but I am.

When it comes to older office, in particular multistory office buildings, the challenge is often looking beyond 'it pays a decent return' and digging in to understand what is required to day to keep vacancies low, and equally or more importantly what will be required tomorrow to attract or keep tenants?

I can tell you that my most difficult or challenging thing is contractors.