We are in a constricted market cycle, low volume, strained budgets, high costs.

If your property management company is good and has built an internal maintenance team which has set rates and had strong relationship relationships with licensed contractor which should keep costs in control, you should never need to shop contractors on your own I wouldn't think.So in short, our policy is give us your preferred contractors upfront if you have them, but then we work all tickets to resolution including dispatch, and payment of invoices.This is of course for operational expenses.  

I'd highly recommend house hacking in your local market since you're in one of the highest cost of living areas in the US, especially if you're renting currently and planning on staying in the area for 5-10 years.It sounds sexy to go out and invest out of state for your first property.

I want to know is it more cost effective or easier to purchase the property alone and put it in a mortgage in our name or purchase the LLC from him that holds the property within it.

So I would say either you need an agent who is a better negotiator than you and justifies their cost or if you value a professional opinion who can double check you.

However, I still struggle to understand the art of estimating rehab costs. 

But me, i will be penalized with the guests relocation costs, according to booking.

The rates are high right now but these loans are limited based on cashflow so you cant take a loan that costs more than you're receiving in rental income.

2- if there is a “problem” Will the “solution” discussed solve it in a cost effective, consumer accepted way?

In total it cost me about $500.Unfortunately, I was not able to reconcile the needs of my niche market with what the Capital Syndicate had to offer.