Generally speaking, how do you approach making an offer when the marketing package essentially says it has little income and it needs significant work?  

My impression is they put a good, entertaining salesman up there to pitch the 3 day event, and reading up on it, it sounds like there would just be more of the same to get you to spend more on the 25k package..

I asked if they would be willing to sell all 5 in a package deal, and they said they would.  

Yes there is some great info and yes there is an opportunity to purchase a training and mentorship/coaching package for between $12K - $40K depending on what you want. 

That is a separate service that is not included in any of the paid tier packages.

Going out of state can work for those people as you can work with people who are able to provide you with everything in one convenient  package in a market that has a much lower barrier to entry then your own.There are downsides of course.

Not to repeat many of the great comments made I'll ad just one point: make sure that the finished "package" works - what I mean is, if your overall approach is to stick to necessary repairs, paint and carpet (and sell the house for 150k) then stick with cheap and easy.

Next you should talk to the local bank and find out what they need in loan request package.

I think the remodel plan is simple flex space with minimal office (1 lobby, 1 private) for a tradesman, so a TI package should be minimal ($2/SF which is nothing more than paint and flooring for tenant turnover). 

I would think that a detailed CSV export would be a standard part of any property management software package.