While you may find a single planner that can sufficiently model your retirement cash flow needs, you are likely to find that a whole lineup of planners / advisers can best serve you in sourcing the broader spectrum of alternative asset classes.Due diligence and sourcing is simply a bottle neck for anyone.

@Matthew Forrest - you asked a good question, and there are three main reasons why I'm looking outside of Lake Arrowhead: first, I'm looking to diversify my properties (to even out cash flow and reduce exposure to any one particular area or type of visitor); second, because I'm looking to have an assortment of places I and my [extended] family can enjoy on occasion; and three, I am looking to build a broader base of knowledge to best serve me going forward.

By seeking out a non local CPA, you expose yourself to a broader pool of CPAs and increase your odds of landing one that is specialized in the area you need assistance with.

This enables me to make larger and sometimes broader investments with confidence and low risk. 

the experience you will get from flipping houses is invaluable and allows you to take a broader perspective on doing deals.If the buy and hold opportunity you're looking at costs you some of your stake to hold, you should think carefully about it.Good luck with your decision!

A self-directed IRA is still an IRA, just with different servicing to enable a broader range of investments.There are a few different types of self-directed plan types and services. 

A wholesaler needs to have a better understanding of improvement cost and ARV and usually require to have a broader connection with people. 

I make sure my numbers are tight on my end and just go with a broader, blanket repair cost based on square footage and condition.

It all depends what you mean by viable and what your objectives are.If you want to buy a property for lifestyle that you would use as a vacation home and rent the rest of the time, you should be able to at least cover your costs, provided that you buy the right type of property in the right place and have it properly managed.As a pure investment, I wouldn't expect very high returns and there are definitely better places for that in the broader region like the Mexican beaches, where properties are generally much cheaper and the potential rental income is much higher.

Besides those groups check out the Black Diamond meeting in Worcester (2nd one in Waltham) as it will give you a broader RE base and great networking.