I have comps pulled, and my next step is to get a contractor/estimator out here to give me a better idea of rehab costs.

But.... how should we handle our next few days of bookings (assuming that the exterminator does say we need treatment for bed bugs [if they say we are free and clear than obviously no action needed]).

If the rental property was your personal residence within the last 2 out of 5 years, it may be eligible for some exclusion.Feel free to reach out with more additional information as I'm happy to help as there a lot of moving parts here.

The draw back when starting out is there can be some cost savings with "bundling" everything together. 

You have to register, but there is no cost associated with that.  

I know exactly how much it should cost to hire a contractor, for any type of work on a house.

Check out FilePlace, where user-created forms are available for free.

All money spend after the sale of the property should be posted to Profit & Loss.And yes on the day of the sale you transfer the pruchase price, loan cost, settlement cost, imporvements to Profit & Loss. 

Often times when reviewing a application I want to check previous rental history and ask applicant the name of previous landlord. i then usually check that with county tax records.

If you'd like to join me as my guest at the next PIN meeting feel free to drop me a DM.