Don't forget that at least at the local commercial level most of these guys and banks know each other so if you get a good relationship (demonstrated by multiple notes with one guy) they see it and it is a confidence level for the second guy as well.I guess my long winded bottom line is develop a relationship somewhere for the first few then expand out. 

When posted the question,  I was more concerned with how easy/difficult it would be to secure conventional loans after having multiple mortgages.  

I would suggest you interview multiple brokers/lenders and get comfortable with someone before you put anything under contract.

So with my end goal being to own multiple rental properties generating cashflow here are my questions:Should I start rehab in the spring and try to list right at the 1 year mark to only pay short term capital gains or wait the full 2 years and pay no tax?

After examining the photos, I could see that this tenant had a cookie sheet against the door of the dishwasher, which blocked the detergent compartment door from flipping open. 

If you use quickbooks payment feature, and you see anything shady going on with bill payments, contact your tenants/clients immediately to verify that they aren’t trying to pay multiple times with the same information.

As such, you can within the 401k have multiple individual participant accounts - one for you and one for your wife - assuming your wife is a documented employee of the business.You could not roll a Roth IRA into such a 401k, but I think you mentioned that your funds were in a traditional IRA.With the 401k, there are still proscribed methods for documenting and bookkeeping so as to independently value your account and that of your wife, but the ability to combine the funds for investments is much easier than in the IRA realm.

Do you have multiple agents working for you?

Let me know if you want to chat offline and run through multiple structure options.  

You have already received multiple responses as to why that is not realistic in the real world - UNLESS you have this secret source of cash Buyers that WILL pay more than the general market!