If that’s the case I may buy a fixer upper to live in with a bigger yard for us and the dog, and maybe do the same there, fix up and rent when I move on or sell depending on what works best.

I would never by a property in an HOA unless it is strictly for yard maintenance.

The purpose of the move is to (eventually) have more living space, a yard and a garage while having a rental offset some of the mortgage. 

Question(s):I’d like to get back into the homeownership game so I’m not continuing to pay high rent and have nothing to speak for it - also, to have more space (ie spare room for home office and guest room, yard, etc...), BUT I’d also like to get into Realestate investing “soon”.

Being a listing agent is so much more than a sign in the yard.

That's why I only invest in my own back yard (which happens to be pretty good).

You then install the window well, include a way to drain the window well (normally connect to existing plumbing or run a drain far into the yard) and repair any drywall on the inside.

Cleaned the yard and made it feel more like a home vs a "rental" property.

It is a 3 bed, 2 bath with a huge back yard and a spacious attic space that we hope to eventually renovate and turn into a 4/3.

Wood is from one of the 800+ trees in my yard.