You need to adhere to the terms of the current lease if there is one. 

I'm a travel RN with a few flips under my belt, one commercial property that turned out well, and am looking to purchase a property in New Braunfels, Tx to live in for potentially 6 months out of the year.

Hi Henry, I'm one of the top agents in the area, I live 5 minutes away in Beach Park.  

One downside is the increased cost of insurance.

I may be a little bit biased, but I believe Chicago is one of the best cities in the country to house hack.   

In general, I price myself 10-15% high outside of my avg lead time, and discount fairly aggressively inside the lead time.This strategy attempts to capture both the planners who will pay a small premium to secure a good data ahead of time, and the last minute deal seekers.In general, it seems many people don’t vary between weekend and weekday pricing enough IMHO.2 ideas I’ve toyed with… in 2+ years I’ve never not booked a weekend.

That should take the most time - determining a realistic ARV and market rent should be the work of just a day or two.If the numbers all work and you've satisfied yourself with the neighborhood, it's time to put one foot in front of the other by making an offer.

I'm trying to verify if this is correct and if so, how much more expensive (ballpark) can the one without standard exceptions be?  

Although I believe I can see the path to my first rental easily, I'm having a hard time figuring out how I'd get to the next one. 

In my market the jump from a 2 to 3 is a big one, 3 to 4 not so much.