The challenge I have with some of the people on this forum though is that they make very direct assumptions and give advice about specific people without ever attending that persons seminar, without ever discussing the program with the person directly or without even discussing the program from someone who has attended the seminar or bought the product.  

if so, what Challenges have you faced here and how did you overcome?

I will be interested to see what the veterans say but I think it will be challenging. 

My wife Lauren and I have developed properties in Greenwich over the past twenty-five years; it was a challenging leaning curve with the vast changes in Planning and Zoning and the increased demands from clients.

Most of the time any websites comps have challenges.

You should be able to purchase up to 5 properties with a mortgage before it becomes more challenging.  

With more challenges to conventional lending, a lower median income than Anchorage, and a little uncertainty in terms of taxation, staying in a rental might have it's appeal for awhile.I remember the decline from the eighties, this is not the same story.  

Each has its own sets of challenges..

You might burn some human capital (like, frustrate your broker/banker/lawyer or the other side) if you go under contract then find something you don't like and don't buy... but obvious I'd prefer to do that than to buying a house with expensive or difficult issues.I know from experience that FHA loans for 3+ family homes can be a little challenging (they have to meet a "self sufficiency" test, where the rents for the units have to substantiate the carrying cost of the property).

One of my greatest challenge tends to be being tactful in explaining why a brick is a terrible life-raft!