The biggest challenge was resolving the parcel recombination, which involved acquiring additional land and coordinating with the city for approval.

Once that has been done I'd like to purchase a property walking distance from myself so I can keep an eye on the property and because I don't have a car.

While its nice to borrow as much as possible, the risk involved can sink someone as in most instances their is personal guarantees involved and lenders will bankrupt sometime to try and get every penny they are owed. 

The potential for a loan call is higher and higher with sub to the more parties you involve if that makes sense.Trying to take down four homes sub to and then do remodels to them all, and then list them on short-term rental sites, and get full permitting and ok for not just the STR, but for your renovations and all prior renovations maybe done without a permit, while on subto, sounds like a pretty big mess to me.I would consult with a sub to specialist and prepare for the potential of having all the loans called at some point.

I'm opening my second home and find them extremely rewarding but think I may stop at these two because I am extremely involved in them and am spreading myself too thin I think. 

A skilled operator can still make money there, but if you are long distance, have no connections to the area, and just like it because it is cheap, it's probably going to take a lot of time/hassle and underperform index funds.

However as with any investment there is risk involved the investor is responsible to conduct their own due diligence.There is an existing property and a lot next door that is a blank slate.

*My Grandma also pays the property taxes; I really have no knowledge of what's going on here with this property outside of people living there rent-free.Next Steps: What are the typical steps involved in initiating a partition action?

A couple of months ago we stayed at a cabin just outside of Hot Springs that was surprisingly nice and within driving distance of the town (we were only passing through).Personally of these three, Broken Bow would rank last but that's only based on a feeling.  

Given this, it's essential to have a real estate attorney involved in the transaction.