One investor in TN shared that flood insurance ends up costing approx $100/month in her area so it really eats into cash flow.

You may have to eat some of the cost just to get this to go away (not that you're in the wrong - you're justified).

Syndication is very much a chicken and egg game. 

Of course HOAs can eat into your cash flow, but could HOAs also be a positive for a first deal, since now I don’t have to worry about lawn, landscaping, snow removal, and big expenses like roofs that could wipe out all my cash flow for the property? 

You do not want to use hard money for something like this as the points and interest carry will eat p the profits fast.There are lots of ways to structure the deal and it will all depend on what the cash contributions and profit potential look like etc.

I received a generous buy out offer, have a nice nest egg in the market, have 3 great renters, and have an interest in a company that pays investment income as well.

Do you think some lenders would have to eat that cost or will it usually be passed on to the buyer?

Right now the rural destinations are eating everyone's lunch but after a vaccine is available and herd immunity takes effect, I'd expect all destinations to pick back up.

You can add a large island with eating on one side and storage on both sides. 

Hey Alex, You need to also take into account the condo fees, it can eat up all your cash flow sometime, especially older condos.