And after the two years I would likely sell the initial house and use all of the profits (tax free) to buy another house to live-in-flip and possibly house hack that one as well.I know I still have a lot of details and stuff I need to figure out but I just wanna hear any opinions on this plan.

If the property does have vacant units make sure you account for the time you will need to fill the vacancy when calculating initial expenses.  3.

Thanks @Ashish Acharya and @Michael Plaks for the answers.I should have been more specific in my initial post.I own my home free and clear, so the new cash out mortgage will be 100% for the LLC.Also the LLC is a multi-members, so it is not a disregarded entity.Can I make a private note to have the LLC assume the mortgage directly, even if technicaly my lender does not allow it?

At the end of the 30 days, if they haven't moved out, you can initiate eviction.  

Not sure how to initiate.

After inspection I made my offer which was below her initial offering price and she accepted.

Which might be OK, if you make great cash flow on it and have paid down your debt principle significantly before selling (not to mention the initial equity that you created through the initial rehab).

I would love a second opinion on if this initially seems like a good deal or not based off the report and then my second question is if there are any creative ways I could finance this.

While initially, this strategy seemed so risky because of the distance and not being able to check in on our investments, I believe that with a few deals behind me, I can leverage the skills I have built building my catering business into building a great support team.

Hope this helps.Partner 150% OwnershipSelect ProjectAgree to Price of Offer and Other Conditions Submit Offer to BrokerAgree to Rehab Plan and Schedule Prepare Funding Opportunity Document Solicit Investors for FundingCoordinate Funding for the ProjectCoordinate Documents with Attorney for Funding Coordinate with Attorney Closing Dates and Fees Coordinate with Real Estate Broker on DetailsSecure Property Insurance and have Utilities Activated Secure Bank Account to Pay BillsPayments over $500 Require Approval of Both Owners Prepare On-Line Advertising for Property Available for Rent Upon Selection of Tenant Run Criminal and Credit Check Agree to Rent Amount and Security DepositProvide Updates to our Private Investors as to Progress of Project and Coordinate with the Bank on the RefinanceRequest Appraisal as soon as PracticalProvide Personal/Business Credit to Secure Refinance Close on Refinance Within Scheduled TimeExit StrategyPartner 2 50% OwnershipSelect ProjectsAgree to Price of Offer and Other Conditions Develop Plan for RehabDevelop Construction Schedule Develop Budget for Rehab Coordinate with Outside Contractors Initiate and Complete RehabLabor will be at cost as part of Participation to Operating Agreement Agree to Terms on Funding Conditions i.e., Interest Rate etcCoordinate Permits if Applicable with Government EntitySchedule Inspections and Remedy ComplianceSecure Certificate of Occupancy or Final Inspection Approval Both Members will Agree to Pay BillsPayments over $500 Require Approval of Both Owners Coordinate Showing Property to Prospective Tenants Select Prospective Tenants and Recommend to Member Agree to Rent Amount and Security DepositClean Up Property for TenantProvide Property Management and Maintenance Provide Personal/Business Credit to Secure Financing Exit Strategy