Choosing between two STR beach properties

[Jake Durell]

I am having trouble choosing between two beach properties for a first investment. 

One set of options are condos in a complex which basically has no beach during high tide and the HOA spends more and more each year remediating that. Fees were $5,500 but may go over $8,500 soon for beach work, but also other worthwhile projects. The HOA seems well organized. These units are anywhere from $160-$200k.

The other options that come up are villas on stilts usually in groups of 3-5 homes. These can be closer to $300k. When these rent, they rent for more money. There's not as many airDNA comps to see how often this might really rent. HOA Fees are basically nothing. Insurance might be as high $4k in CBRA zone though this property seems safer than the condos just outside the CBRA zone. But my wife and I would basically need to take a 90% mortgage to make this work. We'd need to average about 6k in rev after property management costs and any taxes and fees.

This is our first investment property which will be entirely debt financed. We will have a HELOC on our home and a new mortgage on the new property. We could do a villa and maybe have six months of reserves if we are lucky. We could have more with the condo. We likely have no where to go after that other than bankruptcy. I suppose we could try to increase the HELOC but that might be tight.

-Jake