At that point, start stabilizing the properties, proactively spend some cash on big ticket items (roof, furnace etc. that you know are coming due) or upgrades, then start paying them off.

When I start a design project a survey is one of the first items I need (after establishing a program and basic project feasibility). 

Item 1 could be done by the owner and owner selected subs, items 2&3 are typically handled by the builder/GC.

If I were you I would be looking at this as an opportunity to really negotiate price and other items that you want to make happen (credit back at closing, fully furnished and more). 

If I do send a letter or text… what might be the most delicate way to ask a long time tenant like him to leave???

When I've sold items on Facebook marketplace before or given things away using my Buy Nothing group, I've always checked the age of someone's profile and any public info on their profile along with evaluating the conversation to see if they pass a "vibe check".

The structure and roof is good with some issues I want fixed:-covert fuse box to 200amp cb panel-storage shed/garage water damageI’m seeking advice on how to make an offer with either the seller repairing these items (another investor I’m not sure I trust to do it properly) or asking for funds at closing (escrow). 

I will DM you on bigger pockets to discuss a few items, thanks!

My initial criteria is to look for newer built houses to minimize maintenance and upfront cap expenditure on major items like HVAC, Roof, Foundation etc..

All that makes sense and also as an action item I have to keep the dialogue open with our CPA for the 2024 filing considering the deductions.