If your losses exceed your gains, you have a net capital loss for the year.Offsetting Other Income: If your net capital losses exceed your capital gains, you can use the excess losses to offset other types of income, such as ordinary income from wages, self-employment income, or interest income.

Conventional route would work for your 4-unit plan, you on't have to worry about a self-sufficency test going that route like you would with FHA.

Send me a Direct Message and I will be happy to point you in the top neighborhoods to focus on based on your investment goals, criteria and available time you have to spend on real estate investing.

Any advice or a point in the right direction would be greatly appreciated. 

I'm trying to figure out on the naming of this facility as this is going to be much more then just simple self storage and would appreciate some thoughts as some options I'm thinking are     as some keyword and then followed by  storage and yards or should i leave the yards out . like :   safe storage and yards    american storage and yards 

If you mail, be sure to mail to the correct address which can be found on the instructions (first result on google if you google "form 4868")If a payment is due with any of the above, you can include a check with your mailed form, or you can pay directly through the IRS DirectPay system and select "extension" as the reasoning for the payment.

I am wondering if I can go directly to property management companies and buy HOA liens?

I've also done hard money lending, some development deals (build from ground up), self-storage, etc.. 

for this kind of project 4k is sufficient, you may want to ask several handyman/contractors directly.

I wanted to self manage, and hence was thinking of focusing on the areas close to where we live.