@Vic French and @Adam A.

He has two large dogs: 20 lbs French bulldog and 60 lbs pointer.

Also #2, the way you compared LO to a Land Contract is correct. 

Cost of roofCost of decksCost of repairs—4 retro-fit windows, drywall replace, install 4 fan lights, scrape and retexture ceilings, replace weather stripping on 4 French door.

A french drain is easy (other than a lot of digging), but it needs to drain somewhere. 

That makes a lot o sense I never thought about it that way before

I wanted an open feeling where you had easy access to your back yard area through french doors. 

I'm hoping for a favorable appraisal so I refinance to a conventional loan with 20% equity though a higher appriasal value.I have performed several updates including installing a new roof, new aluminum gutters, updating one of the units (kitchen & 1.5baths), french drain system, new paint throughout, etc, etcDo you have any recommendations for a Noob to the refinance process?

I am leaning towards "refreshing" all 3 bathrooms (2 full and 1 half) and then the flooring in the kitchen has some water damage from an improperly installed french door (not by me. was done by the previous owner).

Some ways to prevent flooding in basements or garden units include:1) Keeping your gutters clean2) Extending your downspouts and directing them away from the foundation3) Caulking and weather-stripping the exterior of the property4) Maintaining proper grading so water is moving away from your foundation5) Installing a french drain6) Making sure you have drains at or near the exterior doors.