The harsh reality is that your ten percent is not going to get you very far in commercial property so you may want to consider an office condo - that's how I started - or just run a search on LoopNet for properties you can afford and go after them.

My first RE purchase was a condo, here are some things to consider:-An SFR will usually appreciate better than a condo.

If you still want to consider an HOA property, check out BP podcast #244 with Linda Weygant.

We never (knock on wood) get temperatures that high, but if we did, I would consider an option like purchasing a few of the portable units, but only installing them during those heat waves.

May investors with an 8 unit building will consider an Umbrella over that location.# 2 & 3 are really personal preference and your specific risk tolerance.#4 - I just quoted some 8 units for 2 separate investors and the quotes are coming in just under $2k per year for Replacement Cost and $1M General Liability 

Consider an option though that will also include the added perk of allowing your tenant's on-time rent payments to be reported to the major credit bureaus; this creates just added incentive/point of positive reinforcement to get them to make those payments on time and transition to a system that is easier for you.

It is a bummer that my financing has to be so creative as that means I am not what I would consider an A+ buyer.

In the current market in my area I don't think many people would bother to consider an offer that was not on the standard contract- it would be too much hassle.

Might the Seller consider an even lower Offer than $149k (given the facts)?

But that also depends on what one considers cash flow.Given your limited time, you may want to consider an alternative approach... buying turnkey rentals; partnering with another investor who has the time (to find and run the rehabs) and who is also buy and hold oriented...