It is all fine until things go bad, and the bank decides it has to trim etc. and starts looking for reasons and bad-boy carve outs, then the fine print starts to be real.

New paint, termite extermination and repair, Add trim and baseboards to most of the house.

I covered the cheap counters with contact paper to look like high end marble (~$100), framed the mirrors with trim (~$10 per mirror), upgraded old carpet to vinyl plank ( Lessons learned?

When banks are trimming down, 2nd lien Helocs are often some of the first "fat" to be trimmed.That's partially why we went for a 1st position LOC, as they have the staying power more similar to a traditional mortgage.

With regard to trees, do not expect Tenants to be perform anything more than some relatively low trimming with a simple pole trimmer.

Your going to have to bite the bullet on this one.Any maintenance issue on a property will not be covered by a standard Property policy.Additionally, you could be held liable for damage to the neighbors house if they can argue that you knowingly neglected the trimming/removal of the tree. 

He paints the unit every 12-18 months, ceilings, walls, trims etc.

Mastering little crap like hanging blinds, ceiling /exhaust fans, light fixtures, switches and receptacles, closet doors, doors, screens, screen doors, patio doors, lockset changing and unsticking, smoke alarms, appliances, paint, trim, wall repair, cleaning, etc are the most common needs. 

Install Luxury Vinyl Plank flooring (LVP) throughout both units (Home Decorators Collection Blue Cedar Grey from Home Depot) Install new counter tops and cabinets in 2nd floor kitchen New Vanity/shower for 2nd floor unit Install 3 new windows Install Sump pump in basement Update washer dryer hooks (each unit) Paint all ceilings/walls/ trim ( Agreeable Grey from Sherman Williams) New appliances for 2nd floor kitchen (used from Facebook Market Place)Holding Costs: $8,271 4 months of $1,284 interest only payments Taxes Utilities 6 months Builders Risk/General Liability Premium After all said and done I spent $28,397 (not included holding costs) and was under budget!

$11500Vinyl siding: $10000Gutters/downspouts: $1100Electrical: Remove supply and install new wiring, boxes switches: $12500Doors, interior and exterior and hole will need to be cut for a new window : $5500Partition wall/ drywall and framing: $14000Flooring: fix subfloor as necessary, install LVP $6800Oak trim/ finish carpentry: $10000Demo/ framing/ general construction: $11000Lighting: $1500Appliances: $7000 Then some miscellaneous, profit and overhead and contractor management fee comes to: $40000