Id like 250k available to me to work with, probably spend closer to 200k.

https://www.avail.co/i/Nezd I use Avail for all my needs, great reports, fantastic service does the job and free stuff once in a while.

This strategy probably won't work for the newbie investor who has little or no experience, but for anyone who has been doing this successfully for 5-10 years I see a lot of opportunity.Matt Faircloth wrote a book called "Raising Private Capital" available on this site. 

Although they are harder to find but they are there and capital is more available. 

Much of what is available in our price range are condos and modular homes.

I would make it a goal to walk out of that meeting knowing that you were pre-approved for an amount and also the type of loan programs available to you once you make a decision to acquire a property.

There is also a giant paragraph about how HOA membership is tied to the property ownership and no other methods are available to become a member...but then the Pool Rules go to extreme lengths to single out "occupants", which includes tenants as having no rights to bring guests or use the pool without the owner member being present.   

I think his work is somewhat seasonal so he has some money available and basically just wants to avoid blowing it.

I found 2 available for 100k.

Cash-flow, though possible, is generally not something you'd benefit from here (unless you do it via illegal vacation rental).That said, I would definitely buy a small condo (studio or 1-bed) for myself here, as I'd rather pay myself rather than a landlord, and IF you feel confident enough in doing out-of-state investing, leverage your remaining funds to purchase 1-2 properties that cash-flow elsewhere.If instead you'd rather keep it local, I'd use your available funds to purchase 2 condos, one for yourself and one as an investment.