Once you generate these investor leads, your priority should be to follow up with them regularly through call, text, email and in-person meetings. 

A 1031 exchange costs very little as it fits into your regular closing costs.

Start-up costs are also deductible but are amortized over 15 years with a limit of 5k.Start-up costs have strict rules and your case might not be the same as this one.Case Summary:Timeline line of eventsStarted investigating property: FebPut first contract (canceled): MayBought first property: December 30thWhether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business:Whether the taxpayer undertook the activity intending to earn a profit;Whether the taxpayer is regularly and actively involved in the activity; andWhether the taxpayer's activity has actually commenced.On the basis investor testimony, we may assume that he undertook this activity to make a profit and that he regularly and actively engaged in it.

All a landlord has to do is buy, hold, do the minimum the city requires to upkeep the property, and let time pass.

The taxes, insurance, legal, upkeep, vacancies will drive you nuts if a few hundred dollars ruins your day. ;-) When foreclosures are common, (which they are not right now), I send out two thousand letters a week.

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

It seems like it's something people do on the regular, and the lender doesn't usually trigger the due on sale clause. 

What you've shown here is not really a cause for concern in my eyes, however I see much worst conditions regularly.

I'd focus on getting a better property manager, their job is to shield you from most of these headaches and to prevent them in the first place through tenant selection and doing regular property inspections.

Property Management Company we work with right now to manage is fine with regular rental but I am having hard time working with them on student rental where some of the regular renting rules don't generally apply.