If you're looking for an agency (Fannie/Freddie) type loan (whether owner-occupied or investment), they won't allow your friend to cosign with you since it has to be a close relative for the sameIf you're looking to cross-collateralize your other assets, a local bank/credit union is your best bet since they can be flexible when it comes to specialized financing situations like this Since your friend is willing to cosign, I'd say form an LLC with both of you as members.

A great coach who is physically out there in your area is @Brian Gibbons (Moderators: Brian does not compensate me for recommending him!!)

Now once you have a few under your bet and the contractors know you are serious, they will be more likely to get with you for your estimates.As has already been mentioned, BP has some great guides that can get you moving in the right direction. 

It sounds cheap, but I bet it comes with a lot of headaches.

I figure your best bet is to find several people, so if one is busy or can’t do it or bails, you have other options

@Anthony Wick I'm willing to bet that every single one of us have had an unexpected expense in our lives.

I occasionally input the details into Google calendar week-by-week to help my wife (and business partner) see what's happening and when, but the master renovation schedule for a property is invariably a large physical wall document for me.

I'm thinking vinyl, single hung, double pane will be my best bet. 

Without knowing where the property is, I bet that the units rent for 600+ each in GR.  

I think your best bet would be to house hack your way to 4 properties and then take a "mini" retirement which would allow you to take 6 months off and possibly knock 10-12 countries off your list on one big trip.