Not sure if I have to pay for the more advanced features for it to work better but want to get other thoughts before I start syncing data and have to turn back.Thanks!

The law does NOT apply to landlords:With less then 5 rental unitsThat live in one unit of a duplex and rent out the other unitThat rent out rooms in the home they occupySo, landlords can no longer state in their rental ads, "Section 8 not accepted".The reverse is also true, "Section 8 only", cannot be used.We've always recommended screening S8 tenants the same way as cash-paying tenants.Landlords waiving application fees and/or security deposits only for S8 prospects may also be violating Fair Housing.

Risks: rates go down and you have to pay a prepay of 2 or 3 %; you have to sell and pay the prepay; rents decline & you can't make the payment like any other type of loan; cost upfront a little more than conventional; need to find experienced broker licensed in the state where subject property sits; servicers are bulldogs. 

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

A longer timeline will make paying the extra 2% now more attractive.

We generally advise our clients to go ahead and pay the recapture rates if death is the alternative.The good news about recapture - the deductions are a deferred tax liability to you, and an interest free loan from the government.

The nice thing about the arbitrage business model, is the companies usually pay you a monthly rent, and then they handle all of the AirBNB stuff. 

I have never been disappointed and have actually thought he pays an extreme amount of attention to my needs for the price he charges.

We will be paying nearly $50,000/year in property insurance.

Bottom line: the tenant doesn't get to decide how to pay you.