We are actually seeing some of this in SF where rents are being capped by continued condo supply and appreciation has slowed down vis a vis SFH.

My fiancée and I are both upper class and both drive 10+ year old cars but we aren't unkempt and don't uber to real estate showings.

They may be living with the fiancee’s mom because they could not maintain their own apartment in the past but are not telling you that.

The second application came from another very nice couple who are in the U.S. as legal residents from Europe (they have Visas until 2020).

So I'd like to give a little bit of information about me and what I'm looking for.My fiancee and I currently own 3 rental condos.

we worked through the old owner and tried to get to the kids when ever possible.. all leads were leads until the logs were on the ground.. a few things we did to speed things up  were as posted above and pretty obviouswe set up 1031s  but hard to sell to an 80 year old who could not fathom how that could be legal.and a few did charitable remainder trusts  probably even more complicated and the ones' where we bought those deals I would say the sellers were pretty savvy folks not your typical tree farmer. so as many have stated whats the sellers best interest and your best interest is many times vis a vi taxation not aligned in any manner.

Situation:As a first time home buyer, and first time flipper, Fiancee and I expect a 2 year property to avoid Capital Tax Gain, and allow for time to DIY as much as we can comfortably do.

and my fiancee and I are looking to create about $5,000 a month in passive income, so that I can afford to work less and we can travel together during the summers (which he has off).I'm thinking that I should begin by house hacking since we are currently paying 2,000/mo in rent.  

I just recently renter my apartment to a lady (25) and fiancee (21) less than 2 weeks ago.

@Mary Ann Casey,The properties owned by your IRA can not be covered by the umbrella policy for your personal properties (and visa versa), this would be violation of the IRS rules.