Multiple times projects took so long to get started or to get an appropriate bid, I ended up having to handle it myself (ie. roof replacement, unit turns, etc.) 

Well, can you maybe replace my bedroom set for me and help me get into a new apartment? 

And in doing so I realized that it’s going to be $2k more per year to insure it for replacement value of $145k vs before it was mostly just liability insurance plus a cap of $15k replacement payout. 

Since then, he has had to replace the windows (the seals got old) and now he has to install all new plumbing.

Additionally, I have access to cabinets, doors, and other materials through trades with a friend and uncle who own 100+ doors between them, but still budgeted funds for replacements if they can't offer some. 

Your HOA will likely keep increasing and because of the excessive heat, roofs get replaced more than in other areas and if the HOA is not super liquid, that will come back to you in the form of an assessment.

Purchase price: $179,000 Cash invested: $15,000 Lived in the property for 1 year.Knocked down living room wall, replaced Hvac, floors and gutted and remodeled the kitchen, attic insulation, converted the living room and the dining area into rooms.

Some have sealed batteries and some are replaceable.

They’ve painted, replaced things, upgraded, etc. prolly best the place will ever look.  

I already know I am going to have to replace all of the hardwood floors and probably the subfloors.