Which gives me the idea that I may be able to even delay the subject-to purchase of House 1 until House 2 is finished, if we decide to go ahead with this.I estimated very conservatively.

If you go down this road, plan ahead otherwise there's going to be plenty of headache and possibly, given that you've got family involved, heartache.

If you stick around, continue to learn the fundamentals and come up with a solid plan, you will be lightyears ahead of your peers (you are already ahead of them just by beginning to think about your financial future).

Then when you try to get license they tell you you cant because of zoning issues, luckily I have written documentation of all my registrations county and state, approval from HOA, tax collections, and application for business license and then written go ahead to rent without a license, so we'll see I might get hoofed in the end but at least I tried to comply with the rules.

I feel like its better to come out ahead every time I take a step, then to get beat down.

you have come out ahead?

Now that makes a lot of sense to go ahead with the deal.

That is the key in any vehicle.

If this is a temp fix and you are still going to need to replace the roof soon, why not go ahead and save the $4k and have the roof replaced.From your post it looks like this is a 4-plex building.

Even then, it would be wise to plan ahead how to quickly pay off student debt.