I do recommend a first investment to be something that you can roll up the sleeves and get your hands dirty with, managing everything yourself.

I''m pretty sure there's other repair options like sleeving these types of situations.

You have a fun problem to solve, and as I see it, you have some wildcards up your sleeve!

If it were mine, I'd put in a very small rental office, just a half door walk up with a room for a desk and 8 tall file cabinets (and a half bath for management use).Sleeve A/C and electric heat the office with some benches out front for residents and wanna-renters to sit on.And use the rest of the place as rent-able units, except for maintenance storage areas. 

If you are talking about a window (or a sleeve) A/C unit on a SFH, that seems like personal property (unless it was set forth in the sale agreement to be left behind for you to own).In which case $350 at Home Depot will probably solve that problem.

She rents the bigger bedrooms out to people she knows and she's not afraid to occupy the smallest room or afraid to roll up her sleeves to build that sweat equity.  

So here it is a Sunday , afternoon , and no one is going to be able to come out , so I roll up my sleeves and keep digging .

I got a few decent subs up my sleeve.

I also have a couple great ideas up my sleeve that I would be happy to share with this proposed group, but that I won't be posting on any blog!

If anyone has a name in their sleeve to share, that'd be great.