Personally, I'd never buy the biggest house, or the most expensive house on the street.

The goal is to find a way to offset some of the unexpected W-2 income and pick up of a vacation/rental property at the same time.I like the eastern shore, but I’d really consider your actual goals , if you want to own a 2nd home and use rental income to offset it great, if the only goal here is to save on taxes It’s probably just not worth it.

From the sounds of it, I'd talk to a few realtors and see what it would sell for and put it on the market.

I’d love to chat with anybody like minded or meet up if you’re in the Spring/Woodlands area.Where I’m at currently I won’t be of much use as far as capital goes, but I am a grinder and would love to help any way I can. 

They want to put the listing up live in two days and i'd love to grab it.Can anyone help me get started in the right direction?

From a financial perspective, loading up on insurance is more adventengeous than a LLC because if a claim arises, I'd rather file an insurance claim that give up the equity I built in a lawsuit.

But, I'd guess it's typically way too much.

I'd send a letter to both the neighbor and the HOA informing them that on X day I will be filing suit naming both of them and we can let a judge decide which of them or if both are liable.

Ideally, the property would also have strong appreciation potential.Since I'm new to the area, I'd greatly appreciate any guidance from experienced BiggerPockets members familiar with the Orlando market.

E.g. location, site constraints, your general questionsTo your question, I'd also be happy to hop in with recommendations.