I am a novice here, but am I better off paying down my house and losing the $300 a month PMI, or taking the money I have in the bank and buying a rental?

Rule #1 - Don't lose moneyRule #2 - Don't forget Rule #1!

Doing it with a partner who does this all day is less time-intensive but you lose some control and some of the profit.

Their are two things that matter in this circumstance #1 how many bedrooms the tenants voucher is for and #2 what is their maximum allowable rent that section 8 will allow them to pay based on their income.To your first question If you accept an applicant that has a voucher for $1000 that is the maximum amount that your housing authority will allow you to put on the lease, so in essence you will lose out on the extra $200 a month.

We moved to central Oregon 2 years ago for a Job that went under due to company losing business; since the loss of my job we found a fifth wheel which we lived in for 8 month until a fire which took the rest of what we did own.

And many times, buyers end up paying more if they have contingencies, to win against other cash or non-contingent offers, so I often wonder whether I am actually helping my clients by adding contingencies in this market...I try to disclose as much as possible and explain why we need competent lenders and no contingencies, but I can see that many buyers esp first time buyer are skeptical until they lose a couple of properties they loved over non-contingent offers...And there's no monetary compensation received from my lender whatsoever.

But by doing that, I'd be losing about 43sqft of area.

Any suggestions on what to expect or what action I can take if I lose the bid? 

I'm a local to Fort Myers/Cape Coral, with a 7 year hiatus in the Smokies of East TN, and I am looking to start investing in either area (with an emphasis on SWFL since it's where I'm currently residing).I own a small ecommerce business which I am still focusing on growing, but I'd love to start adding cash flowing properties to my portfolio. 

I have lost friends that i consider family and have also seen what happens to the families when they lose the heads of the households when they did not have anything left for them.