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?

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!

If a vendor purchased multiple truckloads of material at X cost and the market goes down, the material they have on hand is essentially overpriced.  

what starts bogging me down, is the notion that at the end of the  day... you have multiple loans that you have to keep up with? 

He is not a project manager, most small contractors can't handle multiple jobs, they think they could though.