You could consider the areas in the city with the highest value increases.

Would it be worth exploring the possibility of partnering with an investor somehow to help with funding?

If you spend time learning how to manage well, your income will increase, you'll save time, and you'll maintain your sanity with the courage to expand.

It was worth it to just separate out every listing on its own, but if the price keeps going up, we will have to reassess.

Cash flow of $150-$300 per month is pretty common for many new investors, and whether it's 'worth it' depends on your long-term goals.

My duplex - built 1989, 2,060 sf, 2 bed/bath, 1 year old roof, value if I subdivide (county already approved) and sell each separately $150k each ($300k total)Investor duplex - built 1995, 2,300 sf, 2 bed/bath, 5 year old roof, value around $310kThe investors initial request was for an equal trade and they would pay realtor fees, which I replied wouldn't be equal due to buying/selling costs (recording fees, title insurance, closing fee, survey, inspections, loan fees, 1031 fees, accountant fees, repairs), taxes would increase due to new sale price, I'd trade a 3.75% mortgage for a higher one, and I'm on the 10th year of a 30 year loan so resetting that to a new loan would restart amortization and pay more towards interest.

Rents have increased significantly but so have housing prices. 

More eyeballs mean greater viewership, improved SEO, and increased revenue.

In some homes planting the front or placing pots could increase the curb appeal, in others it could be paint or furniture etc.

What are the homes worth?