There’s huge retal income potential if you nail that balance between improvements that wow tenants and improvements that merely look fancy but don’t justify higher rents.I’d also keep an eye on how your high end plan fits the local demand.

Eliminate debt, establish a budget, and save.

It eliminates the need for juggling multiple tools or platforms, making managing finances much more efficient.With two properties, I think Baselane is probably the best option for you.

Whatever market you choose, be sure to nail down your buy box.

During this time, tenant complained of cross contamination, claims got nail in foot while in kitchen - all the same time accessing these areas to take pictures etc.

Using a 1031 to upgrade to a two-family could help you reduce or eliminate the $1,000 out-of-pocket expense you’re paying now.Also, condos often come with HOA fees that limit cash flow, so be mindful of their impact.

I think if you can nail that down you will be able to find a market easier.As a buy and hold investor some of the things that were important to me when deciding on a market were landlord tenant laws, price to rent ratio, housing demand, ability to build a team, large population 500K plus, multi-family availability and some other factors.take the process step by step and you will be fine. 

Anyways, I think @Caleb Brown hit the nail on the head.

That helps you eliminate properties but not decide what to buy.   

Seller Pre-Sale Financing: Consider selling the tenant-occupied property "as-is" now to an investor, perhaps at a slight discount, which could save time and eliminate renovation costs.