Property seems generally stable but owner lost his manager last year and he has health problems.Owner wants to carry paper but needs $100K down to cash out a $72K non assumable loan and $23K in back taxes (4 years). 

If you don't own any property and can have roommates, I would look for a place you can afford. 

This is a great property that we would love to invest in but would like to get some understanding on how we can 1.) afford these capital expenditures early on and 2.) what we could expect to pay for those expenses.

Often times tenants have divorce, car accidents, loss of employment and health issues.One of the things landlords have to be careful about is tenants want to make their problems the landlords problem.First your want to let her know that you are truly sorry that she is having medical problems.If you are wanting to waive some of the rent is totally up to you, but you do need to remind her that she still has financial obligations and needs to see what arrangements she could do to have the rent paid right away.If you have any emergency contacts for her on file youu may want to check with them and see if they are able to help her.I would also recommend that you get a real estate attorney that is familiar with evictions and consult with the attorney.

Once you know what you can afford then get an agent and start looking for what fits your budget and makes good financial sense.

I get an affordable mortgage rate while im fixing up the property.

We still have affordable homes [under $70k that rent for $800+] and lots of jobs and even more renters.With that said, I always suggest looking within an hour or two of your home.  

The Home Affordable Modification Program (HAMP) is 6 years old now, and it’s been extended again.

This isn't really something you can ask too directly, you don't want to seem like you're setting him up to be discriminated against, but if you're observant, you'll notice pretty quickly if he uses home health services, has a social worker, etc.

That also includes non-homestead property taxes, and 10% maintenance.Then I can only afford to put down 5% towards the purchase of the new house.