This will allow you to acquire another investment property with favorable terms (better interest rates, WAY less money down). 5% vs 20% down is massive and will help you acquire more real estate faster in the long run.

There is a legal concept that when a contract is ambiguous that it will be interpreted in favor of the party that did NOT write the document.

I certainly don't owe any favors to someone who is not respectful to the property, their Increases are without a 2nd thought. 

I'm actively thinking about my target areas and possible deals, but would really appreciate if there were any groups or mentors available interested in discussing the ins and outs of favorable market locations, financing, ideal type of investments and getting that elusive First Purchase!

Or would I be wiser to wait until I have a 9-5 post college and just enjoy these years and hope market conditions become more favorable?

Contemporaneous always will win favor in an audit.

To prepare, focus on saving for a strong down payment and maintaining a solid credit profile, as both are critical for competitive financing.If possible, look into FHA or conventional loan options for owner-occupied properties, which may offer favorable terms, especially for first-time buyers.

Some areas offer great potential for rentals and appreciation, while others may be less favorable.

Since they're month-to-month, it might be worth having a respectful conversation, explaining the market situation and any improvements you're planning to make.Some tenants might leave, which could actually work in your favor if you're looking to renovate each unit.

Is there any recommendations for lenders that would do a 90% LTV with favorable terms?