Contribution into an LLC should not be a problem - I'm guessing that you're using a disregarded entity LLC and it's not filing a tax return anyway. 

Expenses can be handled via an accountable plan (if S Corp) or without an accountable plan (if disregarded).Either way, it's highly recommended that you keep contemporaneous written or electronic mileage logs.

Thanks Form tax perspective, your LLC can make payments directly to bank and get tax deductions or you making a payment will qualify for deductions as well.The SMLLCs are disregarded for tax purpose, so both ways are ok. 

I knew this would be upsetting to him but thus far I've been good on all my payments, I fronted materials + first draw before work ever began, I paid other draws and change orders before work was even completed despite the awful communication, delays, and just blatant disregard for deadlines, timelines, and tenants.

Say someone calls me with a property that is ineligible for whatever reason and I tell them their rate is going to be higher by 1-2 points or more.  90% of people immediately disregard that property when they hear that. 

If they are disregarded, and the properties are filed on Schedule E of your personal tax return - then you can combine 1099s, using your SSN (not recommended) or your EIN.

The penalties for not filing are as follows (for 2018)$50 per form if you are late filing, but file within 30 days of the due date$100 per form if you are late filing, but file by August 1$270 per form for filing after August 1 or non filerThere used to be an "intentional disregard" penalty of $540 per form, but I'm not seeing it in this year's regulations.The due date is January 31, but you can get a 30 day extension if you send in the proper form.If the IRS categorizes your rental as a trade or business, it is up to you to prove that it is not. 

For IRS, considered a disregarded entity.

Buying 4 caps"If it's truly a "value add" deal, then you can disregard the going in Cap rate.

Who takes the deduction — don’t care about federal irs position on disregarded entities since LLC’s are State entities subject to a State law regarding their veils...You want limited liability protection afforded by the LLC?