I have gone ahead and filled with my own insurance company.  

Growing up in CAN I already had a head start in the rules, markets, etc, so the learning curve wasn't as long.

Hello,A good rule of thumb in NC I tell my sellers about: if we get lots of showings in the first 2-4 weeks, but no offers, the price is too high by a good bit (15-25% estimated).If we get showings, and one low ball offer, the price is a little too high (5-10% too high).The longer a property sits on the market, the more likely you'll end up accepting a lower price ...better to go ahead and do a price reduction now and sell it faster, than letting it sit and eventually the market will do the price cut for you. 

With an average cap rate on the market of 5.5% (I've sold multiple listings at a 4.8% to 5% cap rate this year) I know that buying at a higher cap rate and CoC, even though I have to wait for my FIG units to be built I will still be ahead of the game in the next 3-5 years because of the better cash flow.  

In declining his offer I would go ahead and set the expectation that you are granting him a promotional rent for this lease period only  and he should expect a rent increase at lease renewal.

Come June 26, 2024, I'll be making a move to your vibrant city, and I'm already thrilled to join the local real estate scene.With 10 months ahead of the move, I'm eager to connect with like-minded individuals, understand the neighborhoods, and explore potential investment opportunities.

This will allow you to have a slower ramp up, have guaranteed tenants day one, and not feel so rushed.

STR's are the most management intensive way to produce cash flow on a property and Tokyo is 9 hours ahead. 

Once you finish the rehab and get a tenant in place, you can go ahead and refinance it again with a DSCR loan if the cash-out amount makes sense

The architect will have a structural engineer they usually use, you can go ahead and use that person or someone else.After that is done, have your architect draft a bid form/template.