As far as how much you pull out it depends on terms.

So I'm guessing it might depend on your state laws and personal situation. and make sure you know of any sticky items that would eliminate the protection you get from the LLC.

As @Carl Millsap said it depends on how much more in rent you're getting compared to the costs of renovating.

Also depends if you are getting appraisal and what attorney charges for creating loan docs

I then plan to do this again or maybe 2 more times depending on the ability to stay under the VA entitlement cap. 

You also have the options of the 2 + 1 which is a 2F with a boarder unit that an owner can live in, but likely can't rent after you leave so it's only a temporary solution depending on how stringent the municipality is.Your VA gives you lots of options, but you won't cash flow if you use at 0 percent down because rates are too high.

I often do a step ladder depending on how severe it is. 

Depends on the Class of the property/tenant.Class A, you may just have occassional maintenance issues.Class B, more maintenance issues, some tenant payment issues, some tenant drama.Class C, a lot of maintenance issues, a lot of tenant payment issues, a lot of tenant drama.Class D, too much to list.

That will depend on the numbers.

Rents for $1,800+ a month, depending on how long tenant will commit.