Perhaps, I suppose that would depend on how well you know him. If I were him I would be more than happy to do it for a promise that you would buy your parts and service from me....seeing as how the only thing on a Harley that is reliable is the glue holding the Harley logo on the bike.
I have had a couple of bikes over the years from Drei, including a BMW R1150GS. He is a nice guy but can sometimes let things slide if you don't keep things going with gentle reminders. However, I have bought a Fazer 1000, a VStrom 1000 and a Yamaha Super Tenere 1200, all new, from Phil (Pipoy) Ang at Caloocan Sales in Manila. Dealing with Phil is a first-world experience, from delivery, through registration and after sales service. Sadly my big bike days are over but he is the only guy I would go to if ever I were to go back to riding. He has a showroom in Makati, a wide range of contacts for people buying and selling and all his bikes, while not the cheapest in town, all come with all taxes and import duties settled correctly. Always my first choice.
That is a big huddle to overcome, how about the second one, getting it registered? Website or other contact information?
Caloocan Sales 340-342 Rizal Ave. Ext. Bet. 7th & 8th Ave. Cal. City 3643652 / 3647967 / 3657274 / 3640982 Caloocan Sales Center Inc.
If he has the connections to deal with customs (known to be one the most corrupt government agencies in the Philippines) I would think that the LTO wouldn't be much of an issue.
As one who has ridden over 28,000.km around every major and many medium & small islands here, for over a year solo, SMALL BIKES RULE. There is zero need here for any bike over 250cc, simple as that. Anything larger is just showing off and limits you severely on banka boat crossings and steep fun barangay roads. See my page on social media.
Sure there is a need for bikes over 250cc. Seems you haven't done much riding on Luzon. You won't get on the NLEX, SLEX or SCTEX with anything less than 400cc. Yeah, you can take the old highways and other side-roads off the expressways.....if you like to ride in urban/ghetto sprawl and sit in traffic. 250ccs turns a 1 1/2 - 2 hour ride into a 5 hour nightmare. It certainly isn't some old scenic route like old Route 66 in the US. BMW XChallenge G650. Goes anywhere your 250cc scooter will go.....plus expressways. Something like that or a KLR 650 (though that is quite a bit heavier than the BMW) is a perfect bike for the Philippines.
Might be worth a look-see at a Authorised Dealer in the Philippines to do a comparison, I am sure they would also have a few Trade-ins on hand; Harley-Davidson of Manila; Home Options Price list; http://dw4i9za0jmiyk.cloudfront.net/2017/05/31/oce6ac651f983d7c497e35f663e38816_ad483d3c25d3.pdf Used Harley's; Harley Davidson Motorcycle Ranking in the Philippines | Priceprice.com Harley-Davidson Used Cars in Manila - Mitula Cars Harley-Davidson Philippines bikes for sale | New & used Harley-Davidson for sale in Philippines