If the home is 100 yrs old, I'm assuming it's a definite gut which is going to require new plumbing, electrical, heating, cosmetics.I spent about $140K reno on my multi family in the heights on NY ave and there were massive problems with it but it was a gut to 3 units & adding 2 bathrooms, 3 brand new kitchens 4 bathroom reno in total, all new flooring, sheetrock , insulation, framing, doors, electrical, plumbing, paint, parts of roof etc.

I'd sell if I were you. 1) I don't like HOAs and certainly not for STR or MTR 2) the numbers don't make sense for you to invest in a big kitchen/bath renovation 3) it doesn't look like it's appreciating very well.

The kitchen counter laminate was also very dated looking. 

The rental had ratty furniture, a record player prominently featured in the marketing but it had no speakers, missing basics items in the kitchen, lots of drunks in the concrete hallways that reverberated right into the bedroom at 2am, a strong odor of urine outside, and more.We have super hosts in this forum that have hundreds of 5-star reviews and are masters of the craft, but I look at their rentals and see they don't have any artwork on the walls, decor is basic, they do nothing to make the guest feel welcome, etc. 

"Ceiling fell in" turned out to just be drywall of the kitchen ceiling.

Maybe you can add clear rules on noise, guests, shared space usage, cleaning responsibilities, maintenance expectations, and specific guidelines for shared bathrooms/kitchen.7.

We improve the kitchen and the patio but just because we live here.

Most landlords will use the remodel clause to remove tenants if they dont want to sell.Just replace the kitchen and bathrooms.

Needs a huge remodel (they put the shower in the living room, and you can't open the oven all the way in the kitchen, absolutely ridiculous).I did check the events and meetups category, couldn't find anything nearby. 

Start with a rental that has modest rehab requirements such as updating kitchens and bathrooms and make sure you qualify for permanent financing through a lending source that offers interest rates similar to that of  a bank.