Prioritizing upgrades on new investment

[Ben Shaw]

Hey BP Community! 

I'm a new investor in the Twin Cities having purchased my 1st owner occupied duplex this past November, and I'm happy to say it's going well so far. I'm looking for some advice on how to prioritize improvements on my property for this year with a fixed budget. See below for specs and list of possible improvements as I see them. Any advice would be helpful, thanks! 

Specs:

Owner pays:

Monthly mortgage: $1493

Utilities: $500/mo

Rental Income:

Unit 1: $1,850

Unit 2: $1,000 (available at the end of the year when we're planning to do our 2nd house hack)

House Projects:

• Repair/replace old windows, some have rotting outside wood. Quoted at $5000 for 3 windows. I have 25 windows.

• Garage is dilapidated and needs new doors framed and installed, bottom plate installed, new siding. Quoted at $5000 to rehab the garage. Currently can't use for parking because the doors are facing the yard (there used to be a driveway but driveway is gone and now alley is behind the garage). 
• House needs painting (I'm not seeing this as a pressing concern necessarily--could wait a few years). 
• Facea needs fixing and painting. 

Budget: $5,000

We've already put in $4,500 for many cosmetic repairs. All of these these things have clearly been issues for a while and they could continue to be issues without creating too much of a problem for the next several years, but I would like to invest some $$$ to preemptively make improvements as opposed to waiting until something falls apart and potentially having to owe more later on. Obviously, as time goes on my repair reserves will build and I can invest more in these things later on, but I'm wondering what would be the best "bang for my buck" right now. I'm leaning one way but with an abundance of counsellors there is wisdom, right? 

I'd appreciate any advice. 

• Thank you all!

[Bruce Runn]

@Ben Shaw- My first advise would be to hire a carpenter to teach you how to put in a window correctly and have him put in 1 or 2.  He could do that in a day and at $55/hour you'd create a huge savings for yourself.   You can buy a replacement window for $200-$300 and put it in yourself if you have 25 of them.  The key is to learn how to do it right the first time and have the tools to do it yourself if you are even a little bit handy.