Single family units are more than plentiful in this area so that was my target, however,  since our recent encounters with multiple hurricanes, insurance makes it near impossible to even remotely turn a profit as a landlord.  

The problem is he has no idea if any of them are worth anything and has now the impossible task of sifting through thousands of items, most of it probably trash, but how do you know without looking up each single one? 

I found out that this was actually not an ideal location, and it has been impossible to rent. 

Take the other half (150k) and buy an already established Storage facility...(300k to build one seems impossible).   

There are so many hidden and fully disclosed fees by the insurance companies that it is impossible to beat the following strategy that I ended up doing and will share with you below: 1) I put a single tenant commercial property under contract with a 45 day due diligence (to inspect the property with no obligation to purchase it) 2) I contacted national tenants (I follow a very specific system) and got one committed to lease the space for 10 years with a NNN lease (NNN means: Tenant pays the lease plus taxes, insurance and maintenance) and a corporate guarantee (lease is guaranteed for the duration and backed by their financing bank like Wells Fargo) and they asked me to spend some money to offset some of their TI (Tenant Improvement for the location) 3) I took the cash I was going to put in to buy in full a WL insurance and instead I just put it as a downpayment for a 20 year commercial loan at very low interest rate and I used some of the money left over to pay for the TI/rehab cost to improve the single tenant retail property as agreed with the national tenant. 4) After we signed the lease the property went up in value from $850k (when it was vacant under contract) to $1.5Mil (with the national tenant in it with the NNN 10 year lease with the corporate guarantee and escalations) 5) My cash on cash was very high and helped me afford double the life insurance coverage for a lower premium because I got instead a level term life insurance with guaranteed sane premium for 20 years) 6) Once the 20 years are over, the loan would be paid off, I would still have the building at even higher value and the rent would easily be at least double what it was when I started 7) I did this approximately 4 years ago and a few weeks ago I refinanced the property and cashed out all the money I had put in, plus some, and I compared my strategy to those whom I know that went for the WL insurance coverage and the financial difference is huge due to the insurance fees, the limitations on what can be borrowed and limitations on income etc etc You can do the same with other type of properties of course.

Also when the weather is bad during hurricane season they will often close the ferry, which can make it impossible to get to the island. 

I am from NY and it is nearly impossible to do a wholesale directly from the home owner. 

This usually results in ridiculously high bids that make it almost impossible to land a good deal through HUD.

Getting a mortgage without a job will be near impossible without going with an alternative loan product that will come with a high down payment and high interest, which is not the "househacking" way. 

Of course, owning an entire house or multi on the East Side is almost impossible - they are very expensive and rarely on the market.