Choosing which project to do first ...

[Donovan H.]

I recently bought a duplex with some fairly expensive deferred maintenance issues. None of the issues are of an immediate nature and I purchased knowing these projects needed to be done within 5 years. I'd like the community's take on how you decide which to tackle first when you can only support 1 major project at a time financially.

1. Roof. Possibly the most urgent. Needs done within 2 years approx. Lowest of 5 estimates runs $8000 in my area. No leaks, but it's on it's last legs.

2. Windows. There isn't a record of last replacement, but they look many decades old. They do not insulate well. Tenants complain about draft and heating costs which they pay. They obviously want this done first. I do not have multiple bids yet. Only bid is $13500 (30+ windows ).

3. HVAC. 2 units. Both are 35+ years old, but have been well maintained and burners replaced within last 2 years. I have not called anyone for pricing yet.

4. Siding. Wood. Old. Unknown if lead paint. Looks ok from curb, but a bit less so up close. One side is blocked from view and this side is pretty bad regarding the paint.

My opinion is the roof is #1 priority, then the rest in listed order. I worry about ticking off my tenants by not prioritizing what they want first. They have lived there for "years" according to previous owner. What do you think?