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.  

Everyone starts somewhere, but it can seem daunting at first.

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!  

As landlords and facility managers, you can’t solve this resource crisis, but you will be challenged to control water waste.By taking the initiative to flush less water down the toilet, you can do more for your facilities’ overall usage.

If the attorney's fees seem unreasonable (ie >$2K) then consult with your own attorney to review and challenge it.  

For the multi family properties, it tends to be a bit more challenging.

managing people/tenants and finding good deals are in my view the most challenging.

I'm finding the biggest challenge is obtaining financing that works for us for our rehab deals.