I have been listening to podcasts on a regular basis.

@Thomas Cundy it’s not clear exactly what you’re asking, but I get the sense that consulting an attorney on this would be a good idea.If you had to evict the tenant I think there’s a good chance you could ask for damages to be added to any judgement you got.A lot depends on the specifics of the situation, for example I don’t know whether you’d need to have something in your lease saying that the tenant is responsible for any damages done by guests or if that’s not necessary because it’s implied.I also don’t know what your options would be against the brother specifically.Assuming that no one is stepping up to fix the damage or pay to have it fixed, and you’re asking how you can get that to happen (and what your options are if they don’t), I do think it’s really a question for an attorney.Since it may end up relating to evicting your tenant, if you have a regular eviction attorney I’d recommend you start there.

I really don't want to go to a regular bank..

Yes you need to inspect - walk through on a regular basis.

I currently have property that has had 3 assessments outside of the regular HOA payment in 3 years.

Don't confuse this with a regular back who happens to have a CRE person.  

Track all of your income and expenses in report form that you understand and invite people you trust to review the report regularly and try to cut expenses and increase income.I could say more personal items as well as business matters that might effect you but I'll quit now,  The more you learn, the more confident you will be.  

Provide an easy calendar/shopping cart that syncs with VRBO and Airbnb (Or at least update it regularly).

Especially when you're investing from out of state - you won't know the market well and you won't be able to see the property regularly - you need to know that the people you work with are incentivized (perfect word, @Jeff Wallenius) to do good work. 

After doing a little more research it seems that portfolio lenders are my best bet for my situation at this point.I am new to all this, can anyone tell me how I can find portfolio lenders in my area and how can I distinguish between a regular lender and portfolio?