On the 3 acre 1216 sqft there are already 3 septic and power are already there and well water.

Normally don’t do a lot of shade or water activities but will find something else to do.  

I had to pay unpaid water bills when the tenant that needed to be evicted up and left.

Wading into the property investment waters.

As it is we both have a strong desire to buy a SFH for ourselves but currently house hacking is a better solution because that other rent is paying our taxes and water and sewer bills and for some mid range priced renovations to the property.

Correct but this will be a STR in a prime market with pool and by beach so I am sure I can manage to break even

A single family will be easier to sell and exit because of a larger buyer pool. 

It seems like if I could put together 3-4 people who are interested in the same deal, and get them to pool their capital together on a flip, you would lower the per-person risk, you would allow more investors to enter the market. 

Hoa is very high, off the water and maintenance is starting to increase.

The structure and roof is good with some issues I want fixed:-covert fuse box to 200amp cb panel-storage shed/garage water damageI’m seeking advice on how to make an offer with either the seller repairing these items (another investor I’m not sure I trust to do it properly) or asking for funds at closing (escrow).