Hi @Joel Florian
Great questions.
1. Should I sell my $400k home in Alaska or try to rent it out?
Depends on how much cash flow or appreciation the home will generate in Alaska, and if $400k could do better for you in Hawaii.
2. Should I buy a 4-plex in Hawaii?
The best performing 4-plexes will be non-conforming homes. Most legal 4-plexes will be in Waipahu, Honolulu, or the West side. Numbers wise, the West side 4-plexes will have the best numbers, but Waipahu has some occasional deals.
3. Should I buy a SFH in HI?
I would definitely recommend doing a live in flip here, especially since you have a good track record doing live in flips.
4. Should I rent for 6 months first?
You could, to help you get to know the area. If you'll be at Schofield, then Mililani is the likeliest place to end up. One of the best neighborhoods on the island. It wouldn't take 6 months to get a good feel for it. Just a few days probably. Good opportunities for live in flips come up regularly.
5. How restrictive are building permits and inspections in HI?
I would avoid building permits if at all possible. It is insane how slow the DPP is at reviewing and issuing permits.
6.
Can I get financing since I have not had a steady job for the last 10
months? ( sold share of contracting business and have been consulting,
doing home inspections, and rehabbing a flip)
It would likely need to be a private lender. I have one we use regularly here, 8.5% and 2 points. But I would at least explore the possibility of getting traditional financing.
7. Will the recent changes to AirBNB legislation in HI affect home prices in the next few years?
I don't think so. Most Oahu units were in Waikiki. The single family homes are scattered throughout Oahu, but mostly on the North Shore and Windward side. I don't think there are enough to cause price drops across the island. If anything it will be specific to certain buildings and neighborhoods.
8. Should I even buy property on Oahu if I intend to move to the big island in 3 years?
If you do a live in flip, then I would definitely buy vs rent.
9. Are there deals in central oahu I could get for less than $500 k cash?
Minimum to get into Mililani will be about $675k. You could get into Wahiawa for about $575k.
10. Should I use a realtor? If so, please recommend one who likes biggerpockets.
I like BiggerPockets. ;) I've worked with quite a few BP members over the years.
11. Should I apply to become an appraiser in HI to learn more about the market?
I'm not sure all that's involved in becoming an appraiser, but I don't think it would be necessary to learn the market. You'll likely want to stick to Central Oahu for live in flips. If you're looking for a rental, then it will most likely be the West side. You can learn these markets pretty quickly.
12. Should I sell my tools and furniture and buy replacements in HI, or ship everything over?
If you're going to ship anything, ship a lot of things, to make it worth your money. Different companies have different sized containers. You'll want to fill whatever container you get. With military moving regularly, there is usually a pretty steady flow of used items being sold. It might be a hassle to hunt it all down when you get here, but it will save on the shipping costs. Also, check to see how long it will take the container to arrive, you might be without your belongings for a few weeks to months. :)
13. If a house is listed as a "tear-down", how hard is it to get a permit to rehab it?
Tear down is a pretty broad description, subject to the specific realtor's opinion. Lots of them are not actually tear down condition. Permits are a beast. There are a ton of homes here that are remodeled without permits, especially if the floor plan isn't being changed. Flooring, paint, cabinets, counters, sinks, toilets, etc.
14. What is the most economical solution to extensive termite damage? Epoxy injection?
Depending on how extensive and if it's structural, the wood will need to be replaced. Termites are a real issue here and buyers will get spooked quickly and walk away, or request to have it replaced. It's better to replace it upfront before listing. If it is something like fascia boards, then there are wood putty-type products that can be painted.