As you go on your journey you're going to need to talk to many people, most of whom won't be a good fit.

People are going to need places to live, especially when they are young and starting out, so there will always be a need for rental housing.  

His tone and implication is that he's going to amend the bill to reduce the potential impact on STR owners -- "The sky is not falling," he's said a few times -- but the bill already has a threshold of 90 days, so when he throws out 60,90, 100 days as some sort of comfort to vacation rental owners, that doesn't make sense to me.

Looking at redfin the last few weeks what i've seen the better deals tend to need some work.

I wouldn't budge much on this, you can't allow them to set the terms, because that sets the tone for the whole relationship.  

Conversely, if you have a slab and the ground settles (which is very common in my area) then you are going to need something to fix the issue (which ironically is . . . piers!). 

However if you plan on growing your business to 10+ properties and doing this professionally then you're going to need to be more methodical about how you run your business from the very beginning. 

Your margins will be less because you’ll have increased costs due to need for management, operating systems, learning curve, accounting, legal and of course cost of capital.Capital can be debt, equity, or a hybrid of both.Start by placing your STR activity under a single legal entity.

Otherwise I will manage the property and flex new business muscles.

Working a full time job while building a portfolio you are going to need people to bring you great deals.