I am in the process of buying property out of state and have run into a series of challenges with the law firm I've been using.

.   ** Remember @Ran Fridman that you are also likely facing recaptured depreciation taxes (25%) and possibly NIIT taxes (+3.8%) on sale, plus state taxes on income (+4.95% for IL). 

I’ll attach a link to a page that describes this in detail as there’s some things to note. https://www.realtymogul.com/knowledge-center/article/what-is...3) who’s your ideal tenant?

But it does vary wildly - I work with a larger firm, we have in house professionals who focus 100% of their time on state and local tax / sales and use tax, various aspects of international, employee benefits, trusts, estates, gifts, etc, in addition to various industry focuses - and as a result we charge higher fees because there is a significant amount of very specialized knowledge floating around that is at our clients fingertips as they need it. 

Most states are land lord friendly and prices are still in a good range to cash flow well. 

Investment Reallocation: Given the negative cash flow from these properties, would it be wise to sell both and reinvest in markets outside of my current state, where positive cash flow is more achievable?

Looking forward to watching your journey and assisting with any out of state investing on your horizon!

Tomorrow I start my 40-hour real estate program to become a licensed realtor in the state of Massachusetts by mid-April 2024.

The State of Hawaii made STR's difficult, however, our workaround are MTR's. 

Varies on the laws of the state you are doing business in, demand, and local zoning laws.1.