For example, I have repeatedly informed him of my very negative experience with ABC Capital Investments (still going on almost one year with no payments to show for it) and yet he continues to promote ABC Capital Investments in Baltimore and Philadelphia despite fully knowing that many people continue to have very bad experiences with them.

Hi @Tim Holt I think in general house hacking is usually a good move because it gets you off the sidelines and into the game with the most favorable financing possible (30 year fixed).There's a lot of value in getting started today vs waiting some undefined number of years until conditions are better, which could be a long time from now, because real estate is a business and the sooner you start actually learning about that business, the better.With all that said, I always recommend that people analyze any potential house hack as a pure investment that they aren't going to live in, because someday they may want to move out and you should know up front (before you commit) whether you're going to be able to do that, or whether you're overpaying and will be stuck in the property unable to move out because it'll be cash flow negative if you do.So you had it exactly right when you wrote, "the property would need to cash flow when I move out and rent out all units."

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Say good bye to the negative connotations of wholesaling, hello to cross selling. 

Idealizing a past scenario is purely negative.

Cashflow is a bit negative on this deal since it's the better part of Tulsa.What do you think?

You will be dealing with low-demographic tenants that qualify for S8 for negative reasons.

I understand the sentiment, but I think it will have more negative effects.The problem is with enforcement.

I would like to invest here but there are two large hurdles: Negative cashflow down paymentI feel that Boston is a fantastic city to invest in.....if you are well capitalized.

Hey @Robert Carmody, we are only on AirBNB and VRBO and they work just fine.I have been reluctant to do a Booking.com listing due to the negative reviews I have heard from other hosts.Booking.com was geared towards hotel stays, which means your STR gets treated like a hotel room.