Contracts exist to protect all parties, and if he genuinely intends to honor his verbal commitments, there should be no issue putting them in writing.

I've had success with bridge loans in the past, but I've always made sure that I had longer term financing verbally committed so that I could refinance early and avoid any complications that may come with this type of financing. 

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.