For larger accounts with PMS integrations VRBO is a passthrough and we are the merchant of record. 

@Fulati PaerhatiRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

There is a catch - the couple wants to 1031 the funds into their sons next larger project which is TBD.

If you're looking at a debt service loan, 15% is the minimum for a purchase but it's much more common (and rates are better) at 20-25%. 

Are you purchasing as investment? 

Quote from @Jaren Taylor: Quote from @Stuart Udis: Depending on the transaction sizes you are pursuing, raising money to purchase property without debt requires either an incredible network of relationships or devoting a lot of time and effort to raising money.

That was an excellent non-answer to my question, Skyler. hihi :)No they are not all the same. some are only interested in dealing with conventional purchases other are as you say better at handling assignments or double closes, some are commercial specialty, etc....A investor friendly one would be, at least from my point of view, one that understands there may need to be some last minute wheeling, dealing, and adjustment made to close a deal, understand what needs to be done and do not freak out about creative deals.Maybe my understanding or thoughts are wrong but that's what I meant by investor friendlyregards :) 

I purchased a fix and flip that got complicated when we found one of the basement walls was bowing in.

I feel a loss of direction and that makes it really hard for me to focus and build.Do we keep at building a portfolio of small multi family (very abundant in my market, very rare to find anything above a triplex for sale), with plans of selling the portfolio and 1031'ing into larger properties? 

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.