I am currently in the market to purchase a tri-plex with the plan to live in one unit, make upgrades, and rent the other two out.

Because if you need to live off the cash flow what you're really looking for is a business. 

basically if anyone has any tips when it comes to researching plots of land in order to make the right purchase i would greatly appreciate it get with a realtor. we underwrite land at no more than 10% of after built value. in our market we build under the average new build value which is about 515k. we like to be around 420-450k and smaller footprint about 1500 sq ft with attached garages. we build close to urban core where everyone wants to live and net migrations match up. but suburban is fine. if you give more context I can help but in most markets land is a buyers market. most people aren't looking at it or buying it. 

I would like to enter the landscape of real estate investing, but the area I live in has a barrier to entry with regards to cost.

Right now I'm living in Baltimore, still working 9-5 W-2.

I think I'll start out where I live and probably branch out outnof state once I build my knowledge and experience. 

Quote from @Brendan Doherty': I’ve read in books of people getting past having to live in the property they own so they can rent all units year one of ownership(living on the property with an rv).

JeffWe lead a couple investor meet up groups in person and live stream about the Central Ohio real estate market.

Having a property management company seems to be a good option for me since I am living out of state.

Furthermore, it aligns with the growing trend of home improvements that enhance daily living while maximizing investment returns.