Yes, it's taking longer, but I'm still saving more than what the carrying costs are.  

It's not uncommon to see 3 or 4 individuals bunk up and share a house to save money, most of the time I will encourage it to someone who is afraid to live on their own.The Biggest Challenge?

I initially considered the 203k, but my broker advised to do the conventional due to saving on the pmi and extra hoops to jump through with the FHA loan.

Whatever you pay your PM, assuming their good, is worth it because they’ll save you a lot more money down the road.

I’ve found that for the time investment it requires, I really don’t save that much doing it myself since I’m less efficient than the pros are.

I have talked to the Hendricks County Assessors office a few times and it sounds like if you designate a property as a rental with the county they say it can (depending on the area and the current assessed value) save you money on real estate taxes. 

My backup plan is to purchase more condos (~200k/each) which gross about 45k/year (net just over half that) and save up until I can afford something bigger.Ideally I want to stay in the same city with the multi and do a combination of long term and short term rentals.Thank you for your time.

The problem is if you calculate the long term interest savings, it takes many years to even break even on the larger upfront interest payment.

Its payed for (with our savings) and we are still waiting to have the remodel completed and to get lit eased, the estimate for the lease given to us was $700 to $850.

Buy a multi family with low money down, rent out the other doors so your mortgage and other expenses are paid for, essentially you’re living for free and saving a lot of money.