Second, the reason for buying during a dip is to take advantage of lower prices, but there's no guarantee that the dip in a few years will be BELOW current prices. 

While we are advancing in the market cycle and are now certainly in the second phase of the seller's market I don't quite see the turning point on the horizon.

Either 1 or 2 of those people took a loan against the property and defaulted, the first by taxes and the second by default to the bank. 

Plan is to live in it for a year or so as I do the work it needs.The second one, it is a two family.

I know there's a million ways to skin a cat and it comes down to personal preference, but my CPA seems so adamant about not paying my house off that it has me second guessing doing so.

I went out of state (Kansas City) last second and glad I did, it's worked for me so far.... and in theory had I deployed the capital needed to make a mortgage same as my rent I'd EASILY be able to cover my rent and then some.I will lose the appreciation game, but I was never into that for investing anyways... plus I have the freedom to move as needed when life happens IF I need to even if that's not on the table now.

One of my biggest questions going into my first purchase is, how can I get my second, and what does that timeline look like.

Second, owner payments were taking too many steps to process which was creating a lot of work for my staff.

Second, I have a single member LLC that is wholly owned by another single member LLC. 

I started have seconds thoughts about her after she misses a couple of the showings at the beginning.