Does the replacement property sales price need to be higher than what I sell the SFR for?

Looking to continue the adventure to replace income as we head toward retirement. 

How much you keep is up to you, but I don't have a high W-2, so I make up for it in reserves that could cover major expenses (enough to replace roofs on several properties at once) That's for my peace of mind being a single parent running a business.

This is extremely helpful for the tax savings benefits but also because many of the assets used in a restaurant business need to be replaced much sooner than 27.5 years.Some of the major benefits of Cost Segregation are:Reduction in real estate taxesReduction in casualty and property insurance premiumsFor previously misclassified assets, you will now have the opportunity to claim any “catch up” depreciationBy accelerating depreciation, you increase your cash flowHaving additional cash allows you to invest that money back into your business, invest in other opportunities or pay down your mortgageHere’s a list of personal property that could qualify for accelerated depreciation:Drive-throughCanopies and awningsFlooringPoint of sale systemsDecorative millworkKitchen equipment hook-upsDoorsEquipment installationHVACWiringBeverage equipmentFood storage and preparation equipmentFloor coveringsSignage site improvementsInterior light fixturesFire protection equipmentThese studies should be conducted with your cost segregation specialist, CPA and financial advisor.

Is that different between contractor and inspector and how much cost to hire them to inspect give me report total cost for repair or replace like electrical systems or plumbing or roof ? 

Even a blind person is only allowed one guide dog at a time, except for short periods where a new dog is in training to replace the old dog.

HVAC replaced within the last 5 years, electrical upgraded to 200 amp service, updated middle of the road fixtures and flooring. 

I made a 5 year plan to replace my current income and will hopefully be able to leave my current day job and pursue these types of investments (and larger ones!)

HVACs break, roofs leak, basements flood, storms cause damage, carpets need replaced, tenants cause damage, tenants don't pay, etc. 

She is now again willing to turn in keys for cash but our offer seems less exciting given the circumstances (vacancy/leasing cost/replacing stolen items adding up).