During the time we lived there we made some minor upgrades/repairs- renovated upstairs bathroom, replaced carpet on 1st floor with LVP flooring, added artificial turf to the backyard, replaced pool pump, and replaced the HVAC system.

Market price was at 650K, the deal might only make sense to purchase at $438,782 (Including CAPEX/Repairs funds).

A client whom wanted to sell her home but was under water due to needed repairs vs current market condition How did you finance this deal?

Do you do wraps, subj-2, lease w/option to purchase, CFD, Owner Fin, SDIRA, Owner financed 2d mortgages, Joint Venture the deal where you bring some capital and maybe help with repairs and sell and do splitsies, ....  

No matter how well you plan, there will always be unforeseen issues – from hidden structural problems to unexpected repair costs, or project delays.

The other property was vacant for awhile during repairs so I owed money…which my property manager charged me two bills for but she never forwarded it to the water company, this was in 2022, then tenants moved in and owed more.

If that's the case, you should be able to repair it, without replacing the entire roof. 

I wasn't unprepared—I had a clear idea of my MAO,  ARV, and estimated repair costs.

I've also spent $10k on repairing what I thought was a foundational issue (it turned out not to be).

The security deposit will be used to repair any such damages or any other obligation against said security deposit including but not limited, to unpaid rent."