Id say an investor friendly agent is also a realtor specifically being a part of lobbying for landlords rights through being a major investor, a local public policy committee member, taking advantage of the doors that the associations open to speak directly to legislators. 

Landlord or Tenant Friendly State legislation 6.

Once you own more than 4 doors in a community or 2 in states you don't live in, it is worth it to have a professional, as that is when new legislation in areas will have a higher risk for you as a landlord.If you are a personality that does your own business, and private taxes, repairs your own car, manages your own rental flips and finances properties on your own, then you more than likely don't need a management company.

Units in Cleveland do well too, but I personally wouldn't buy an STR in Cleveland proper until this legislation gets sorted out. 

However, due to lumber prices, fence installation is quite expensive and uncertain if I should move forward with this request.

If you are uncertain, have a professional management company work with you.

Also spreading the risk over more doors will protect your capital during uncertain times.

I know how to calculate profitability using the Enemy method, and I know I’ll have to research legislation, but identifying a high cash flow area is overwhelming.

Here is link to landlord friendlily states based off their legislation.  

She's 75 now and it is uncertain if she would be able to still live on her own long enough be safe from Medicaid forcing a sale to cover her long-term care expenses.I've considered buying it from her and she pays me rent, but there seems to be some legal issues with that.I've read some comments about a trust, but any insights would be welcomed.