Likewise, you will also not be losing if you recapitalize the current investment property by stretching the term at a higher interest rate so long as you leverage that equity into another deal that increases the overall ROE.

I will say that as a tenant, it was nice to not have to worry about anything, to have the flexibility to up and move to another city when the lease expires, and to have the ability to remain mobile.I don't think it's a stretch to argue that Millennials are less interested in owning property than previous generations.  

Plus, I'm just not thrilled about forking out 20% when I would rather put that money to work for me elsewhere and opt for a 5-10 percent down payment.So in the simplest terms, if one uses math and logic, we clearly have the means to afford the house, but with traditional financing, the 20 percent will be a bit of a stretch for us.  

If I add that large expense I could probably get $1200 but that might be a stretch. 

In addition, for almost a year I have been working as a residential construction manager which has significantly stretched my knowledge on dealing with contractors, scheduling projects, managing job sites, and learning every step there is in new construction. 2 years ago (when I was 21) I made the decision that I wanted to develop a future in real estate, and every step since then has been building towards that goal.

I don't think demand for $100k primary residence will be strong in that area, there are so many 1950s ranch houses $60-70k, even though yours is the nicest.From an investment standpoint, that area is a stretch to rent over $925 on a 3 bdrm.  

he'll just need an addendum and all contract documents to state he has the ability to move in within the 60 days.The risk if it's tenant occupied is he might have to evict if he legally purchases and the tenant does not vacate.75 days move in wont work I'd stretch out the escrow by burning time till you're within 60 days or restructure the contract:

As I said above, the seller has managed this property for many years and has apparently not treated it like a business, i.e. having long stretches of vacant units while he took his time in making any needed repairs or maintenance.

I felt like I was on hold with my search because I didn't want to start making offers on other properties and stretch too thin with my cash or ability to get a loan.

But I would try and make sure you have enough reserves to survive a multi year bad stretch where rents plummet.