An umbrella policy will cover multiple things, such as secondary coverage on your personal liabliity, secondary coverage on your auto's, as well as multiple homes, both primary and rental, business pursuits, recreational vehicles, farms and equipment, vacant land.

So this is a secondary issue, but it is also important one.

So, if it needs roof, flooring, paint, etc and contractors total quotes come to $10K for easy math.  

Ditto Chris Martin most commercial lenders are portfolio lenders thus they keep their loans in house and don't sell them in secondary markets.

But even then, especially considering the fact that you are paying more interest than principal for the first several years, it seems like it would be a long time before the equity on those four properties would amount to something that you could refinance and pour into more or bigger purchases.According to the math in this super simple (and probably flawed) example, the investor would be earning around $7200 in cash flow a year (before tax), and building equity in his properties.

My math with these new rents has me renting out the 2BR and 3BR for $950 and $1200 respectively, me living in the 1BR, and after mortgage/taxes/insurance/utilities I would break even if I bought this for $280k.

I'm estimating the secondary building to be worth $75,000+ if the parcel could be split and sold as two pieces.

Not for the faint of heart ti manage themselves. i recently helped a client purchase a JEWEL, that he will be out of for under 35k and will have aection 8 tenants beating him up to hand him their 3 bed vouchers. (1400 a month)....do the math.

You'd just have to do the math for the various scenarios

You do the math and you have a negative cash flow of 250/mo with even considering vacancy out of equation (assuming 0% vacancy).