So, again, an opportunity to take on less risk initially to get the learning curve out of the way.Bottom line - your approach doesn't have to start out one or the other. 

So I give the bill to my PM and they bill the tenant and they reimburses me.

If you plan on eventually selling, central air would add a significant value increase, so you may consider if that's the case. 

@Cloey Green there are so many different ways to think about and evaluate markets.

We love the chalets and the town of Breckenridge but just wondering if the Chalets would still be a good investment even though they're priced so high ? 

The bank will put a hold on them, so you can't just draw them out, so don't plan to need them for a while.This will cost you an appraisal on both properties to be performed by that lender. 

My biggest mistakes that have cost me dearly have all been contractor related, so my advice would be to vet your contractors as much as possible. 

so, to recap, you need cash for: down payment + closing costs + holding costs.for a new investor, a live in flip might be a lower risk option than an outright flip. 

So, I did.

I'm looking for an experienced contractor to partner with on my first full flip; I own two properties and have done minor renovations to those properties but this is my first full flip with a full rehab so I want someone with experience to assist as I learn the ropes.