Best thing to do is avoid the higher DTI debt to income, claim one as investment and use the rents to offset the new purchase. 

Also, most Umbrella Policies only pay out if your underlying policy pays out, and the underlying policy will do everything they can to find an exclusion or that you were negligent (which you probably were) in the cause of action to get out of paying the claim.

They may justifying paying more by claiming they’re paying the premium for the “business”, but since the “business” and the real property are inseparable the property owner will still benefit from the increased value due to the arbitrager efforts.  

Yes a partnership tax return will probably run roughly $500; however, it ensures everyone is claiming the correct amount and not drawing the others for audit.

The HOA has acknowledged the roof issue but claims repairs are delayed as they’re still collecting bids.

The claim is that it didn't expand in Portland so they feel there will be no problem and they will extend it indefinitely.

You claim to receive no remuneration for this from the syndicates you are pitching- but only time will tell if you're the only guy not getting paid to raise money for others.

For higher-end properties in Cincinnati, everyone seems to claim they can handle it, but then there are performance issues. 

I did file a large claim a few years ago for a broken HVAC.

I am no professional here, just explaining from my experience.. first, insurance starts claim and they send adjuster out to assess, check damages, and collect documentation.