Personally, I don't lose sleep over sized of earnest money deposits when I'm the seller.  

(SFH vs MFH, size, lot, etc...)  

If it means that you're not very good at conceptualizing what needs to be done, and how much it costs, you should have someone good assist you/do it for you, even if it means hiring someone (depending on the size of your business), because getting the math wrong will mean the difference between success and bankruptcy, and this is even more true the further down the ladder you go in terms of profit margins. 

There's also a nice size garage on the property that I would be using for my vehicles I store, if I cleared it out at some point, that could be rented as well, possibly could look into a separate meter, garage has its own driveway its separate from the home.  

Yes, if you choose to do this, you will need to learn about w2, taxes, insurance costs, time sheets, audits, all that good stuff of being an employer, which the insurance agent should be able to provide.

It has a small 2nd structure on the property that used to be a 2nd garage that someone finished off and now is living area ( am not sure the exact size but I am looking into it.  

So yeah when I can I live in Mid Town Manhattan for 10K per year versus taking on a mortgage in the same area for a comparable sized condo or co-op for 750K, which equates to $3100 Plus maintenance of at least another $1000 then I am much better off with a 10K a year lease.

However, I just started calling around and it sounds like my husband needs to have 12 months left on his military contract OR have documentation from a new employer in the same field as his prior MOS (job in the military) if it is less than 12 months.

The truth is income is a messy topic when you venture into the calculation of over time, commissions, self employment income, rental income, and other grey areas of how income is calculated.

My income, after all, is all from employment, so it's pretty straightforward.