They make it pretty easy to self manage once things get rolling.

Once it is up and rolling it is pretty easy for a single property.

Not sure in your area but 200K should be enough to get the ball rolling. 

After that, all rental losses are blocked and pushed into future years.

How do they know if this is an owner stay that you blocked on your website, and it pushed over to Vrbo?

Get it rolling immediately.

I am hoping to roll these two into one loan and reduce my monthly payment/ interest rate on the HELOC as I will be having the debt long term.I also currently own a 11 spot RV Park which I own all 11 units and is currently generating $10,375/month in rent.

If the appraiser pushes back, point out that there are old houses in some markets that have NO rooms with 7' ceilings and therefore 0 sq ft of GLA but OBVIOUSLY those houses are still livable and still have a value.

This is my first purchase (don't want to do anything stupid) and the rents could swing 600/month depending on what I'm allowed to do in the basement - I'd be in the red from a cashflow perspective if I can't duplex them.Am I rolling the dice here / do you not typically find out for sure until you close and begin renovations?  

Only downside is Roth IRA cannot roll into a 401k.