Like late fees and yard work.We also go over how to operate a house.

Our home received damage last month due to a wind storm which tore shingles off the roof and tore a part our fencing, requiring re-shingling and we have decided to rip out the entire old fence and put in new fencing and enclose the yard. 

Needham is an incredible market, and depending on the location in Needham it might have some yard space? 

You could send a cleaner every month that reports the house is fine, only to find the dog dug up the yard, chewed off the sprinkler heads, and scratched up the exterior doors.

I just showed a house the other day to a prospective investor and the neighbor on either side had this sign in their yard.  

Driving through the neighborhoods you're interested in for yard signs is time consuming but may be helpful. 

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”.