It's in Florida, has great view , close to disney attractions!

What are the prospects for value increases in this area?

Tenants often appreciate transparency and may be more understanding of future rent increases if they are aware of the property's maintenance challenges.Consider a Sale or 1031 Exchange: While you've expressed concerns about commission costs, it might be worth re-evaluating the long-term benefits versus the immediate costs.

My first concern as a tenant would be that you are going to increase the rent in month 2. 

She will get each beneficiary to sign off on allowing this to happen, lessening their inheritance cash-wise but keeping the family in a home.My idea is that the trustee daughter could purchase the home, but could do so instead through a sort of owner-financing where the Trust finances the asset to her directly rather than buying it in full at great cost and taking out a mortgage on an already paid for property:- Property is in Trust and is fully paid off,- Trust finances the property to Trustee for closer to market value, and payment can still be set at 1500- No/less down payment required- Any interest rate, maybe 0- Tenant family makes rent payment of 1500, which pays off the property and pays into Trust- Beneficiaries' % share accrues gradually as payments are made- Set future balloon payment if necessary (if Balance required at a certain time, for college, etc.)This would decrease the out-of-pocket cost for the Trustee purchaser, and increase the amount that each beneficiary will receive (eventually).I have no Trust experience, though, and I'm hoping to hear from the experts.

In Lake Tahoe many condos are experiencing huge increases in HOA to cover increases in insurance and cap ex and many owners are selling. 

But I wouldn't go breaking the bank on anything there especially if you wouldn't see a drastic increase of what Section 8 may be willing to assist the tenant with. 

I learned about finding a deal which should have positive cash flow but it seems increasingly impossible in today's market, especially in Austin TX area.

I just want to check with the group, are you finding the same challenge with getting an umbrella insurance with increase amount of properties.

It increases complexity and cost dramatically and thus should be avoided.Whether you need an LLC at all and other legal protection issues - now that indeed is for attorneys to answer.