We strategically improved the property with minimal investment, focusing on cleaning and minor updates to enhance its market appeal.

To improve the deal, consider increasing rents, negotiating the purchase price, improving financing terms, reducing expenses, considering long-term appreciation, or house hacking fully.Good luck!

For direct bookings, you've got to improve your SEO ranking on Google. 

I've dealt with a lot of tenants like this in the past and if they don't act professionally from day 1, I've never seen it improve. 

A marginal producer isn't likely to improve if you increase it's cost of finance.This is where you would sell and 1031. 

Once I became more financially secure I stopped investing for cash flow, only started buying good buildings in good areas and my life significantly improved.  

1. use the 1031 money to buy 2 investment properties with a combined values >= the sales price2. use the 1031 money to improve one of my existing investment properties (e.g. building an ADU / remodeling)Thanks

I would sell the properties.4 rental properties over 3 years won't make you much money.Maybe 100 per door per month in cash flow and a matching amount in appreciation.That is $9,600 over a 3 year period assuming you have SFH's.You are improving your ability to make more money in a better position hopefully when you complete your master's degree.You will make that $9,600 working 2 weeks.The sale of the home will hopefully allow you and your wife be stress free for those 3 years helping you make a higher hourly rate.

Are you looking to make improvements or buy as-is?

If you build your own, you can continually improve and refine it as needed.