Do not have this conversation at 8:00 PM on a weeknight after a long day.

A rider allowing for using your owner-occupied property as a short-term rental for a specific/limited amount of time is very different than an investment property being used as a short or long term rental 100% of the time.Also, telling your home insurance company that you STR your home occasionally does not give you extra coverage for those types of risks, it simply means if your renter burns your home down the insurance company isn't going to immediately deny your claim. 

I did not come back to revisit this post from so long ago.I did not buy this property. 

Pretty hard with a W2 job, but very possible... just takes too long.

I have an opportunity to make a quick 30k in equity, but only cash flow around $25 — if I look at long term appreciation, that seems to make sense to me, but am I overlooking something and trying to make this work?

If your project takes 4 months instead of 2 by hiring a GC it may end up costing more in the long run.

However, long story short, yes there is, although I would recommend finding an advisor who is skilled in holistic financial planning that includes not just traditional stock market investments or real estate investments exclusively, but all investment strategies to help in your specific goals.In general though, you can either find a fee-only CFP that has expertise in real estate and other alternative investments, or you can find an advisor who is at the very least willing to have a conversation free of charge prior to any actual investments so they can give you a very good idea of whether they would be able to help you prior to beginning a relationship.

Best response about LLCs that I've read in a long time.

I took too long to make some decisions regarding design and it slowed me down.

I'm m focused on staying disciplined and maximizing cash flow, so your suggestion on BRRRR and DSCR loans is especially valuable as I plan my long-term strategy.