We have had offers of $430K on it few months ago as was.

We DO plan to offer these marketplaces in future years, and hope to meaningfully cut down on situations like this (although you can never fully avoid them). 

ANYONE can put in an offer.

I would recommend speaking with a mortgage broker that can assist you with both the purchase and refinance 

Tools like LegalNature offer templates and document storage for compliance purposes.

I usually need them 9-5, so I'll offer 40 hours guaranteed.

Key west offers the highest of $1,786,950.00 and Naples-Marco Island slightly above $1.4M. 

Is anyone aware of a more near term fund that offers cashflow earlier on and isn't a full development cycle fund?

For example, in FL you must have a land trust or you're paying a lot of money in for an LLC, but in Ohio land trusts don't offer asset protection and an LLC isn't taxed as heavily. 

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.