I'm running into a similar issue.

If you bought one of those with 2nd home type financing (should be better terms than an investment property) and pay the >$2,000 in taxes and ~$300/month HOA fee you are around $1200 a month which is probably more than a similar place will rent for.If you want to go a house for sure then the lowest place is a full rehab/ tear down listed at $260K (only 2br and 700sqft).

Is this deal similar to your first four properties or have you refined what you're looking for?

Someone from a post made a similar comment:http://www.biggerpockets.com/forums/52/topics/93343-purchase-in-my-name-then-transfer-to-llc-or-buy-with-the-llcIs this true?

@Jacob Patterson I had some what of a similar decision to make several years ago.

In another word, is your bid more favorable if you do not have mortgage contingency vs. another similar one (maybe slightly lower offer) but without mortgage contingency?

I have a similar situation. 

If you become a paid member on here for PRO on BP there is a program that does something similar for valuation although it does not have near the functions that this program has.

Surely someone on BiggerPockets has been in a similar situation so hopefully there is an easy answer to all of my questions.

I have a similar backstory and totally relate.