I've flipped several properties in Eastwood Hills East and surrounding neighborhoods, with about half selling to homeowner occupants and the other half sold to investors with tenants already in place.That said, the specific property you're considering is key.

Some strategies to lessen the negative cash flow are: house hack and rent out the other unit as a mid-term rental (to traveling professionals or for people temporarily displaced because of insurance reasons like fire) or short-term rental (business or vacation).

You will only be entitled to the deductions directly tied to the property, such as interest, taxes, insurance and maintenance. 

But today with Dodd Frank this would be totally illegal to sell to homeowners without going through QM process. 

Home values have been rising, and you may reach this amount sooner than you think. 2. can you lower your homeowner's insurance?

I have an agent sending me properties and I have ran the numbers on dozens of properties, but the crazy high taxes and insurance have killed every deal I've analyzed.  

I run sum numbers for you please see comments below before refinancing and post refinancing .If I were in your position, I would approach it as follows:Initial Investment Assumptions: Market Value: $360,000 Purchase Price: $360,000 Equity: $0,000Financial Breakdown: Hard Money Loan (LTV 100%): $360,000 Interest Rate: 10% (30-Year Amortization) Monthly Payment: $1,995Upfront Costs: Origination fee (1%): $3,600 Closing Costs (3%): $10,800 Renovation Costs: $10,000 2 Month of Carrying Costs During Renovation: $5,390Total Upfront Required: $29,790Total Capital InvestmentPurchased price $360,000 Upfront Costs $29,790Total: $389,790To make this investment work, you need to rent the whole property for at least $3,165/month, refinance it let say after one year with 5% interest with a traditional mortgage.Year One Rent: Monthly Rent Income: $3,165 Monthly Rent Losses during renovations (2 Months): -$6,330 (-$527/month distributed over 12 months) Total Rent Income: $31,650 per year => $ 2,638 per monthMonthly Expenses: Hard Money Loan Payment (10% Interest): $1,995 / per month interest only Property Tax (Assuming $3,000/year): $250 per month Property Insurance (Assumption): $100 per month Utilities (Hydro, Gas, Water): $292 per month Assuming 0% Vacancy first year Assuming 0 % Repairs & Maintenance first year because unit has been recently renovated Total Monthly Expenses: $2,637Monthly Net Cash Flow: $1Post-Renovation Refinancing Strategy:So far, we’ve purchased the property, completed renovations, and rented it out.Next, you can approach the bank for a refinance to consolidate your initial investment of $29,790 plus your 360k debt into a mortgage.

For expenses like utilities, property tax, and insurance, I estimate a 3% yearly increase.However, keep in mind that if you do renovations in the first year, it’s likely you won’t need the full 5% repair allocation for the first or even second year.

@Jay Garrison grand is still the solid boarder, even if your west of Homan as long as north of grand there’s solid tenants/homeowners.

Landlord shall be responsible for paying any Homeowners Association(HOA) dues and property taxes for the Property.I was wondering if I should add a additional rent clause for the sewer just so I have my base covered in case tenant try to get "smart" with the lease.I think you're fine if that's in your lease to bill them.