Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

We closed the LLC because it was not giving us protection since the properties and mortgages are under our names instead of the LLC, so it was extra work and cost for no benefitQuestions:1-I assume we need to issue 1099 for these contractors even though we are not incorporated, right?

So, maybe do 30-50% down, for better cashflow and make sure you have reserves for mortgage payments in case there's a rental market dip in the future.DM us if you have any more questions:)

I do have a monthly mortgage on my property and have this as a starter home.

Not much to add to the good advice already written, exceptYour mom could easily get a reverse mortgage to pay for her care, then you and your brothers could split the equity left upon sale.

I also broker mortgage notes. 

With rates high, I don't see much changing in the market as buyers struggle to afford a mortgage. 

Consider duplexes or triplexes that can help offset your mortgage and provide steady income while you figure things out.

Obviously the HOA is keeping values in this neighborhood down because an owner would have a mortgage plus another $715/mo for the HOA, which only covers use to a community center but nothing else.Besides holding costs, is there anything else I should be concerned with for a flip on a land lease? 

You can have multiple conventional mortgages and have a great credit score as long as you don't pay late or get too close to the maximum debt to income ratio.