I would love to own some mid-long term rentals in the near future, but am not quite ready for the time commitment to that yet. 

Has anyone dealt with similar “last-minute” habitability disputes where tenants change their minds after committing?

Have a local appraiser or experienced investor sanity-check your after-repair estimate before you commit.2.

That is if he gives a Sh t. 

However he is totally swamped between all his customers and commitments as he’s been in business 45 years so I have been trying some new guys to try to take some stuff off his plate.

Quote from @Marc Winter: @Sai T.

What’s more important is that they have experience working with real estate investors and a proven track record in tax and accounting for your specific type of investments (long-term rentals, short-term rentals, syndications, etc.) .Reviews can definitely be helpful, but I’d still recommend having a one-on-one call first before committing.

Even keep some in stock, bonds and t-bills in a low fee index fund (that is boarderline sacrelidge on this site but since you already have a good nest egg good to stay diverse)2.

We always dot our I's, cross our T's, and have the proper documentation.

They can share what to watch for and potential off-market deals.If you want, I can give a quick checklist of what to inspect and questions to ask the seller before committing.