"normal" is very relative to location and timing, was it normal to find cashflow in 2020/2021?

When it comes to determining whether nail holes are considered normal wear and tear, it often depends on the size and number of holes, as well as local laws and customary practices.

In NH/NE, having a solid RE attorney who understands entity structuring and estate planning will be a huge asset — a lot of investors here recommend asking your CPA for referrals since they often work closely with attorneys.As for pivoting with purpose, many investors in your shoes start by clarifying whether they want to optimize for cash flow, appreciation, or lifestyle flexibility — that decision usually shapes whether they lean toward multifamily, short-term rentals, or commercial.

For your own home, think lifestyle first (pets included).

My brother-in-law wants us to buy him out so he can use the money to fund his lifestyle and potentially buy himself a condo in the city.

Y’all have a great lifestyle down here. 

I have the opportunity to turn my first home into a STR once moving into a new home. I have read all the blog posts, etc but would rather talk numbers with someone in a similar situation/in my area. I live far west of...

What you are feeling is normal, mainly in today's era.To achieve financial freedom in your early 20s, involves building a strong foundation of positive habits, strategic planning and good financial habits that will set you up for long-term success.

In order to overcome those limitations, you would have to either drastically change your business model to short-term rentals (which sometimes may not be feasible at all or may be detrimental to your business) or drastically change your lifestyle (such as one of you quitting your W2 job and becoming a full-time investor.)  

@Henry Clark Hey Henry, living on a boat in San Diego is definitely a unique lifestyle!