Or the roof has major leaks which has caused significant damage to the decking and the ceiling is crumbling (So now you need to add new roof and decking to the budget).

I would assume you would want to budget for roof 25 year life span, hvac 20 year life span, appliances and hot water heater 12 year life span, bath and kitchen remodel 15-20 year life span, etc.

So without more info on the property (address or at least zip code, age of the property, condition of the various components such as roof and foundation, among other things), it will be hard for others to gauge the reasonableness of these assumptions or provide specific feedback. 

I just feel like a gift card out of the blue is a really well-intentioned idea, but could actually send the wrong message (and sets a different tone for that relationship altogether).

I do have some large expenses coming up in the next few years such as replacing the oil boiler with a gas boiler (the basement floods a increasingly and the oil boiler is oddly the lowest point intentionally) and the roof is probably 5 years out maybe a little longer.I’m grateful to be in this position and honestly got very fortunate with how the cards rolled out on this one.

If the roof falls apart 3 months after you close, will saving $200 a month really do anything to pay for it?

This reno consisted of more cosmetic but did require some electrical, plumbing, new windows, and roof repairs.  

It's hard to gauge the reasonableness of these assumptions without more info on the property (address or at least zip code, age of the property, condition of the various components such as roof and foundation, among other things).I see you've budgeted $0 for repairs. 

I owe 65k and the value of the home was 90k before I put a new roof on.

Definitely going to need a property manager around the Dover, TN area.